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Here is a chemical reaction formula: Reactants are amine:CC(C)N1CCNCC1, amount is: 0.001769999973475933 MOLE;aryl halide:CCOC1=C(C=C2C(=C1)N=CC(=C2NC3=C(C=C(C=C3)F)F)C(=O)OCC)Br, amount is: 0.0008859999943524599 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.002219999907538295 MOLE,this reaction does not need solvents,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 8.859999798005447e-05 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 4.4299998990027234e-05 MOLE.Products are 0:CCOC1=C(C=C2C(=C1)N=CC(=C2NC3=C(C=C(C=C3)F)F)C(=O)OCC)N4CCN(CC4)C(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of ethyl 6-bromo-4-(2,4-difluorophenylamino)-7-ethoxyquinoline-3-carboxylate (400 mg, 0.89 mmol) and 1-(Isopropyl)piperazine (254 µl, 1.77 mmol) in dioxane was added cesium carbonate (722 mg, 2.22 mmol), tris(dibenzylideneacetone)dipalladium(0) (40.6 mg, 0.04 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (55.2 mg, 0.09 mmol). Reaction vessel in oil bath set to 110 °C. 11am After 5 hours, MS shows product (major peak 499), and SM (minor peak 453). o/n, MS shows product peak. Reaction cooled, concentrated onto silica, and purified on ISCO. 40g column, 1:1 EA:Hex, then 100% EA. 289mg yellow solid. NMR (EN00180-62-1) supports product, but some oxidised BINAP impurity (LCMS 655). |
Here is a chemical reaction formula: Reactants are amine:CN1C=NC2=C1C=C(C(=C2F)N)C(=O)OC, amount is: 0.007619999814778566 MOLE;aryl halide:C1=CC=C(C=C1)I, amount is: 0.009139999747276306 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.01899999938905239 MOLE,Solvents are Solvent:COC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.0007619999814778566 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.00030499999411404133 MOLE.Products are 0:CN1C=NC2=C1C=C(C(=C2F)NC3=CC=CC=C3)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (441 mg, 0.76 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (279 mg, 0.30 mmol) were added to a round bottom flask which was evacuated and flushed with nitrogen 3 times, anisole (16.600 ml) was added and the mixture evacuated and flushed with nitrogen 3 times and then heated to 50ºC for 10 minutes. Cesium carbonate (6204 mg, 19.04 mmol), methyl 5-amino-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxylate (1700 mg, 7.62 mmol) and Iodobenzene (1.023 ml, 9.14 mmol) were stirred in anisole (33.2 ml), the flask was evacuated and flushed with nitrogen three times and then heated to 50ºC. The catalyst mixture was transferred into the flask with the reactants (by syringe) and the mixture heated to 100 °C for 18 hours. The reaction mixture was diluted with isohexane (60 ml) and the solid collected by filtration and washed with more isohexane (30 ml). The solid was slurried in DCM / MeOH and adsorbed onto silica then purified by flash silica chromatography eluting with 2% 3.7N NH3 / MeOH in DCM to give methyl 4-fluoro-1-methyl-5-(phenylamino)-1H-benzo[d]imidazole-6-carboxylate (1310 mg, 57.5 %) as a yellow solid. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC=C(C=C1)I, amount is: 0.008059999905526638 MOLE;amine:CN1C=NC2=C1C=C(C(=C2F)N)C(=O)OC, amount is: 0.006719999946653843 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.01679999940097332 MOLE,Solvents are Solvent:COC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.0006719999946653843 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.0002690000110305846 MOLE.Products are 0:CN1C=NC2=C1C=C(C(=C2F)NC3=CC=CC=C3)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (389 mg, 0.67 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (246 mg, 0.27 mmol) were added to a round bottom flask which was evacuated and flushed with nitrogen 3 times, anisole (14.900 ml) was added and the mixture evacuated and flushed with nitrogen 3 times and then heated to 50ºC for 10 minutes. Cesium carbonate (5474 mg, 16.80 mmol), methyl 5-amino-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxylate (1500 mg, 6.72 mmol) and Iodobenzene (0.902 ml, 8.06 mmol) were stirred in anisole (29.8 ml), the flask was evacuated and flushed with nitrogen three times and then heated to 50ºC. The catalyst mixture was transferred into the flask with the reactants (by syringe) and the mixture heated to 100 °C for 18 hours. The reaction mixture was diluted with isohexane (50 ml) the solid collected by filtration and washed with more isohexane (25 ml). The solid was slurried in dichloromethane (40 ml) and methanol (10 ml) and filtered, washing the remaining solid with more dichloromethane / methanol. The filtratre (containing product) was evaporated onto silica and purified by flash silica chromatography, eluting with 2% 3.7N NH3 / MeOH in DCM. Pure fractions were evaporated to dryness to afford methyl 4-fluoro-1-methyl-5-(phenylamino)-1H-benzo[d]imidazole-6-carboxylate (1316 mg, 65.4 %) as a light yellow solid. |
Here is a chemical reaction formula: Reactants are amine:CN1C=NC2=C1C=C(C(=C2F)N)C(=O)OC, amount is: 0.006719999946653843 MOLE;aryl halide:C1=CC=C(C=C1)I, amount is: 0.008059999905526638 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.01679999940097332 MOLE,Solvents are Solvent:COC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.0006719999946653843 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.0002690000110305846 MOLE.Products are 0:CN1C=NC2=C1C=C(C(=C2F)NC3=CC=CC=C3)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (389 mg, 0.67 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (246 mg, 0.27 mmol) were added to a round bottom flask which was evacuated and flushed with nitrogen 3 times, anisole (14.900 ml) was added and the mixture evacuated and flushed with nitrogen 3 times and then heated to 50ºC for 10 minutes. Cesium carbonate (5474 mg, 16.80 mmol), methyl 5-amino-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxylate (1500 mg, 6.72 mmol) and Iodobenzene (0.902 ml, 8.06 mmol) were stirred in anisole (29.800 ml), the flask was evacuated and flushed with nitrogen three times and then heated to 50ºC. The catalyst mixture was transferred into the flask with the reactants (by syringe) and the mixture heated to 100 °C for 18 hours. The reaction mixture was diluted with isohexane (50 m) and the solid collected by filtration and washed with more isohexane (25 ml). The solid was slurried in DCM / MeOH and adsorbed onto silica then purified by flash silica chromatography eluting with 2% 3.7N NH3 / MeOH in DCM to give methyl 4-fluoro-1-methyl-5-(phenylamino)-1H-benzo[d]imidazole-6-carboxylate (1510 mg, 75 %) as a light yellow solid. |
Here is a chemical reaction formula: Reactants are amine:C1=CC(=CC=C1N)S(=O)(=O)N, amount is: 0.03579999879002571 MOLE;aryl halide:CC1=NC(=C(C=C1)OC2=CC(=NC=C2)Cl)C, amount is: 0.02759999968111515 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0027600000612437725 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.0027600000612437725 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.001930000027641654 MOLE.Products are 0:CC1=NC(=C(C=C1)OC2=CC(=NC=C2)NC3=CC=C(C=C3)S(=O)(=O)N)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3-(2-chloropyridin-4-yloxy)-2,6-dimethylpyridine (6.47 g, 27.57 mmol), Sulfanilamide (6.17 g, 35.84 mmol), CESIUM CARBONATE (13.47 g, 41.35 mmol) and XANTPHOS (1.595 g, 2.76 mmol) were stirred in DMA (130 ml). Purged this stirred mixture by bubbling nitrogen through for an hour, then added the Palladium acetate. Heated to 130ºC in a metal block (block at 150ºC) and held at this temperature for 3 hours. LCMS (monitorbase) then showed DP as MH+ = 370.99 and MH- = 369.03 at 1.82 minutes, 84%. Allowed to cool to room temperature. The reaction mixture was evaporated to dryness at 50ºC giving __ a dirty-yellow solid residue. Treated with 150 ml water and the resulting yellow solid filtered off and washed with water. Dried by desiccation under high vacuum over phosphorous pentoxide at room temperature to constant weight. This afforded 11.98 g pale- yellow solid [A]. LCMS(monitorbase) showed it to be DP as MH+ = 370.99 and MH- = 369.03 at 1.83 minutes, 90%. _ _ This material was crystallised from acetonitrile; dissolved up in ~1 litre boiling acetonitrile and the cloudy solution filtered hot through a fluted paper. Crystallisation of product from the filtrate was eventually achieved, with difficulty, by rapid cooling in drikold/acetone and seeding/scratching as it warmed up. Cooled in ice/water then the solid was collected by filtration and washed with chilled acetonitrile. Dried by desiccation under high vacuum at room temperature to constant weight. This afforded 6.03 g creamy-white solid [B]. LCMS (monitorbase) then showed DP as MH+ = 370.99 and MH- = 369.03 at 1.49 minutes, 96%. Material B was combined with the same product from P14-A and this total of 7.32 g recrystallised from the minimum of acetonitrile (~550 ml) with hot filtration again to remove trace insoluble matter. Cooled in ice/water and seeded/scratched to induce crystallisation then stood in the fridge overnight. The solid was collected by filtration and washed with chilled acetonitrile. Dried by desiccation under high vacuum initially at room temperature, then at 60°C, to constant weight. This afforded 5.04 g creamy-white solid [C]. LCMS (monitorbase) then showed DP as MH+ = 371.06 and MH- = 369.08 at 1.85 minutes, 99%. Unfortunately nmr showed entrapped acetonitrile at an unacceptable level (~0.5 equiv.). To remove this material C was stirred in ~100 ml ether for an hour, recollected and washed with ether. Dried at 60°C as before to constant weight. This afforded 4.73 g creamy-white solid [D]. |
Here is a chemical reaction formula: Reactants are amine:C1=CC(=CC=C1N)S(=O)(=O)N, amount is: 0.055399999022483826 MOLE;aryl halide:CC1=NC(=C(C=C1)OC2=CC(=NC=C2)Cl)C, amount is: 0.04259999841451645 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.004259999841451645 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.004259999841451645 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.0029800001066178083 MOLE.Products are 0:CC1=NC(=C(C=C1)OC2=CC(=NC=C2)NC3=CC=C(C=C3)S(=O)(=O)N)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: XANTPHOS (2.466 g, 4.26 mmol) was added to 3-(2-chloropyridin-4-yloxy)-2,6-dimethylpyridine (10g, 42.61 mmol), Sulfanilamide (9.54 g, 55.39 mmol) and CESIUM CARBONATE (20.83 g, 63.92 mmol) in DMA (200 ml) at 20ºC. Nitrogen was bubbled through the reaction mixture for 1 hour then PALLADIUM(II) ACETATE (0.670 g, 2.98 mmol) added. The suspension was stirred at 130 °C for 3 hours. The reaction mixture was filtered then evaporated to dryness. The residue was triturated with water (150 mL) and filtered to give crude product as a cream solid - 90% pure. The crude solid was triturated with hot acetonitrile (300 mL) and filtered to afford crude product as a cream solid - 98% by LCMS. This was combined with the product from EN02084-31 and dissolved in boiling acetonitrile (approx 1 L). The solution was concentrated to 500 mL and cooled to ice bath temperature with stirring. A precipitate formed which and the suspension was stirred at room temperature overnight. The solid was filtered to afford 4-(4-(2,6-dimethylpyridin-3-yloxy)pyridin-2-ylamino)benzenesulfonamide (12.00 g, 76 %) as a cream solid. |
Here is a chemical reaction formula: Reactants are amine:C1=CC(=CC=C1N)S(=O)(=O)N, amount is: 0.011099999770522118 MOLE;aryl halide:CC1=NC(=C(C=C1)OC2=CC(=NC=C2)Cl)C, amount is: 0.00851999968290329 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.000846999988425523 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.000846999988425523 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.0005789999850094318 MOLE.Products are 0:CC1=NC(=C(C=C1)OC2=CC(=NC=C2)NC3=CC=C(C=C3)S(=O)(=O)N)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3-(2-chloropyridin-4-yloxy)-2,6-dimethylpyridine (2 g, 8.52 mmol), Sulfanilamide (1.91 g, 11.09 mmol), CESIUM CARBONATE (4.17 g, 12.80 mmol) and XANTPHOS (490 mg, 0.85 mmol) were stirred in DMA (40 ml). Purged this stirred mixture by bubbling nitrogen through for an hour, then added the Palladium acetate. Heated to 130ºC in a metal block (block at 150ºC) and held at this temperature for 3 hours. LCMS (monitorbase) then showed DP as MH+ = 370.99 and MH- = 369.03 at 1.83 minutes, 83%. Allowed to cool to room temperature. The reaction mixture was evaporated to dryness at 50ºC giving a light-green solid residue. Attempted to partition this residue between DCM (~50 ml) and saturated aqueous sodium hydrogen carbonate (~50 ml). The insoluble matter was filtered off and washed through with water, then DCM. This dirty-yellow solid was dried by desiccation overnight. Wt = 2.04 g. LCMS showed it to be DP, 94%. This material was crystallised from acetonitrile; dissolved up in ~150 ml boiling acetonitrile and the cloudy solution treated with a little Norit SX4 decolourising carbon. Filtered hot through a fluted paper. Slow crystallisation of a creamy-white solid occurred on cooling to room temperature. Cooled in ice/water then the bulky solid was collected by filtration and washed with chilled acetonitrile. Dried by desiccation under high vacuum at room temperature overnight. This afforded 1.29 g creamy-white bulky solid [A]. LCMS (monitorbase) then showed DP as MH+ = 370.99 and MH- = 369.03 at 1.83 minutes, 99%. |
Here is a chemical reaction formula: Reactants are amine:C1=CC(=CC=C1N)S(=O)(=O)N, amount is: 0.035999998450279236 MOLE;aryl halide:CC1=NC(=C(C=C1)OC2=CC(=NC=C2)Cl)C, amount is: 0.027699999511241913 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0027699999045580626 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.0027699999045580626 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.0019399999873712659 MOLE.Products are 0:CC1=NC(=C(C=C1)OC2=CC(=NC=C2)NC3=CC=C(C=C3)S(=O)(=O)N)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: XANTPHOS (1.603 g, 2.77 mmol) was added to 3-(2-chloropyridin-4-yloxy)-2,6-dimethylpyridine (6.5 g, 27.70 mmol), Sulfanilamide (6.20 g, 36.01 mmol) and CESIUM CARBONATE (13.54 g, 41.55 mmol) in DMA (130 ml) at 20ºC. Nitrogen was bubbled through the reaction mixture for 1 hour then PALLADIUM(II) ACETATE (0.435 g, 1.94 mmol) added. The suspension was stirred at 130 °C for 3 hours. The reaction mixture was cooled to ambient temperature and filtered then evaporated to dryness. The residue was triturated with water (150 mL) and filtered to give crude product as a cream solid which was 90% pure by LCMS. The crude solid was triturated with hot MeCN (300 mL) to give a solid which was collected by filtration and dried under vacuum to give a cream solid (7.86g) which was 95% pure by LCMS. The solid was dissolved in the minimum amount of boiling MeCN (650 mL) and filtered to remove remaining trace solids. The filtrate was concentrated to approximately 400 mL and stirred at ice bath temperature until a precipitate formed. The suspension was stirred at room temperature overnight then filtered to afford a cream solid (6.4g) which was 100% pure by LCMS. Combined with EN02084-42 to get a single larger batch. |
Here is a chemical reaction formula: Reactants are amine:CC(=O)N1CCNCC1, amount is: 0.0057299998588860035 MOLE;aryl halide:C1=C(C=NC=C1Br)Br, amount is: 0.005200000014156103 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.015599999576807022 MOLE,this reaction does not need solvents,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.0006249999860301614 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.0005200000014156103 MOLE.Products are 0:CC(=O)N1CCN(CC1)C2=CC(=CN=C2)Br, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3,5-dibromopyridine (1.233 g, 5.20 mmol), 1-(piperazin-1-yl)ethanone (0.734 g, 5.73 mmol), PdOAc2 (0.117 g, 0.52 mmol), XANTPHOS (0.361 g, 0.62 mmol), Cs2CO3 (5.09 g, 15.61 mmol), 1,4-dioxane as added to a 10 mL microwave vial. This was degassed and refilled with N2 and then heated at 140 °C in microwave for 1h. LCMS showed reaction done with the peak at Rf1.24 showed a fragment mass of 284. Evaporated solvent. Residue purified by ISCO (0-20% MeOH in EtOAc )to get the desired product 1-(4-(5-bromopyridin-3-yl)piperazin-1-yl)ethanone (0.470 g, 31.8 %). Trial # 1: 3,5-dibromopyridine (407 mg, 1.72 mmol), 1-(piperazin-1-yl)ethanone (231 mg, 1.81 mmol), PdOAc2 (38.6 mg, 0.17 mmol), XANTPHOS (119 mg, 0.21 mmol), Cs2CO3 (1681 mg, 5.16 mmol), 1,4-dioxane as added to a 10 mL microwave vial. This was degassed and refilled with N2 and then heated at 140 °C in microwave for 1h. LCMS showed reaction done with the peak at Rf1.22 showed a fragment mass of 284. Evaporated solvent. Residue purified by ISCO (0-20% MeOH in EtOAc )to get the desired product 1-(4-(5-bromopyridin-3-yl)piperazin-1-yl)ethanone (118mg, 24%). |
Here is a chemical reaction formula: Reactants are amine:C1=CC(=CC=C1N)N2C=CN=C2, amount is: 0.00043700000969693065 MOLE;aryl halide:CN1CC(OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3, amount is: 0.00043700000969693065 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0013099999632686377 MOLE,Solvents are Solvent:COCCOC, amount is: 0.0 ,Catalysts are metal and ligand:C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4, amount is: 4.3700001697288826e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 4.3700001697288826e-05 MOLE.Products are 0:CN1CC(OC2=C(C1)C=CC(=N2)NC3=CC=C(C=C3)N4C=CN=C4)C5=CC=CC=C5, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: [Reactants], 8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.120 g, 0.44 mmol), Palladium(II) acetate (9.81 mg, 0.04 mmol), 2-(Dicyclohexylphosphino)biphenyl (0.015 g, 0.04 mmol) and Cesium carbonate (0.427 g, 1.31 mmol) in DME (2.5 mL) were placed in a microwave vial and flushed with argon. The reaction mixture was then run in the microwave at 100°C for 1 hr. Reaction not complete. Run for another 30 minutes in the microwave. Still not complete. Added 0.1 eq of Palladium(II)acetate and 0.1 eq of 2-(Dicyclohexylphosphino)biphenyl and let the reaction mixture run in the microwave for additional 45 minutes. Reaction complete. The reaction mixture was filtrated through celite and the filtrate was concentrated. The crude product was purified by preparative chromatography giving 0.072 g (41%) of the product. N-(4-(1H-imidazol-1-yl)phenyl)-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine |
Here is a chemical reaction formula: Reactants are aryl halide:CC(=O)N1CC(OC2=C(C1)C=CC(=N2)Cl)C3=CN=CC=C3, amount is: 0.00014200000441633165 MOLE;amine:CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC, amount is: 0.00016999999934341758 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0004250000056345016 MOLE,Solvents are Solvent:COCCOC, amount is: 0.0 ,Catalysts are metal and ligand:C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4, amount is: 1.4199999895936344e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 1.4199999895936344e-05 MOLE.Products are 0:CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(CC(O4)C5=CN=CC=C5)C(=O)C)C=C3)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1-(8-chloro-2-(pyridin-3-yl)-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)ethanone (0.043 g, 0.14 mmol), Palladium(II) acetate (3.18 mg, 0.01 mmol), 2-(Dicyclohexylphosphino)biphenyl (4.96 mg, 0.01 mmol) and Cesium carbonate (0.138 g, 0.42 mmol) were placed in a microwave vial and flushed with argon. DME (2 mL) was added and the reaction mixture was run in the microwave at 100°C for 60 minutes. No product according to LCMS. Added 0.1 eq of Palladium(II) acetate (3.18 mg, 0.01 mmol) and 0.1 eq of 2-(Dicyclohexylphosphino)biphenyl (4.96 mg, 0.01 mmol) and flushed with argon. Run in the microwave at 100°C for 30 minutes and the reaction was complete. The reaction mixture was filtrated through celite and concentrated. The crude product was purified by prep-HPLC. The solvent was evaporated and partitioned between sat. NaHCO3 and dichloromethane. The organic layer was separated, dried (MgSO4) and concentrated giving 0.0234 g (35%) of the product. |
Here is a chemical reaction formula: Reactants are aryl halide:CN1CC(OC2=C(C1)C=CC(=N2)Cl)C3=CN=CC=C3, amount is: 0.00023600000713486224 MOLE;amine:CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC, amount is: 0.0002589999930933118 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0007070000283420086 MOLE,Solvents are Solvent:COCCOC, amount is: 0.0 ,Catalysts are metal and ligand:C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4, amount is: 2.3599999622092582e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 2.3599999622092582e-05 MOLE.Products are 0:CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(CC(O4)C5=CN=CC=C5)C)C=C3)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: [Reactants], Palladium(II) acetate (5.29 mg, 0.02 mmol), 2-(Dicyclohexylphosphino)biphenyl (8.26 mg, 0.02 mmol) and Cesium carbonate (0.230 g, 0.71 mmol) were placed in a microwave vial and flushed with argon. DME (2 mL) was added and the reaction mixture was run in the microwave at 100°C for 60 minutes. Reaction not complete. Added 0.1 eq of Palladium(II) acetate (5.29 mg, 0.02 mmol) and 0.1 eq of 2-(Dicyclohexylphosphino)biphenyl (8.26 mg, 0.02 mmol) and flushed with argon. Run in the microwave at 100°C for 60 minutes and the reaction was complete. The reaction mixture was filtrated through celite and concentrated. The crude product was purified by prep-HPLC. The solvent was evaporated and partitioned between sat. NaHCO3 and dichloromethane. The organic layer was separated, dried (MgSO4) and concentrated giving 0.029 g (28%) of the product. |
Here is a chemical reaction formula: Reactants are amine:CC(C)(C)OC(=O)N, amount is: 0.0010499999625608325 MOLE;aryl halide:C1=CN=C(C=C1F)Cl, amount is: 0.0010000000474974513 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 7.999999797903001e-05 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 7.999999797903001e-05 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 3.9999998989515007e-05 MOLE.Products are 0:CC(C)(C)OC(=O)NC1=NC=CC(=C1)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-chloro-4-fluoropyridine (132 mg, 1 mmol), tert-butyl carbamate (123 mg, 1.05 mmol), CESIUM CARBONATE (652 mg, 2.00 mmol) ,TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM (36.6 mg, 0.04 mmol) and 9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE (46.3 mg, 0.08 mmol) were suspended in 1,4-dioxane (2.5 ml) ,degased with argon and heated to 90 °C for 4 hours. After cooling the reaction was quenched with water and extracted with ethyl acetate ( x 2 ). The combined organic phases were washed with water , a saturated aqueous solution of brine , dried over magnesium sulfate , concentrated then purified by preparative HPLC using a Waters X-Bridge reverse-phase column (C-18, 5 microns silica, 19 mm diameter, 100 mm length, flow rate of 40 ml / minute) and decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. The fractions containing the desired compound were evaporated to dryness to afford tert-butyl 4-fluoropyridin-2-ylcarbamate (41.3 mg, 19.46 %). |
Here is a chemical reaction formula: Reactants are amine:COC1=C(C=CC(=C1)C=O)N, amount is: 0.037700001150369644 MOLE;aryl halide:C1=CC2=NC=C(N2C=C1)C3=NC(=NC=C3Cl)Cl, amount is: 0.01510000042617321 MOLE,Reagents are Base:C1CCC2=NCCCN2CC1, amount is: 0.001509999972768128 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.001509999972768128 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.0003769999893847853 MOLE.Products are 0:COC1=C(C=CC(=C1)C=O)NC2=NC=C(C(=N2)C3=CN=C4N3C=CC=C4)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3-(2,5-dichloropyrimidin-4-yl)imidazo[1,2-a]pyridine (4 g, 15.09 mmol), 4-amino-3-methoxybenzaldehyde (2.281 g, 15.09 mmol), 9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE (0.873 g, 1.51 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM (0.345 g, 0.38 mmol) and 1,8-DIAZABICYCLO [5.4.0] UNDEC-7-ENE (5.64 ml, 37.72 mmol) were dissolved in Dioxane (120 ml) then degazed and purged with argon. The reaction was heated to reflux (bath 120°C) for 2H30. Reaction mixture was filtered through a filter cup and concentrated. FR01132-77-01 w=14.65 g The crude product was purified by flash chromatography (NOVASEP) on silica gel ( 15-40µm ) eluting with 0 to 5% methanol in dichloromethane. The solvent was evaporated to dryness to afford 4-(5-chloro-4-(imidazo[1,2-a]pyridin-3-yl)pyrimidin-2-ylamino)-3-methoxybenzaldehyde (34.9 %) as a clear yellow solid. PBO-01132-77-02 w=2 g |
Here is a chemical reaction formula: Reactants are aryl halide:C1COCCN1CC2=CC(=C(C=C2)Br)F, amount is: 0.0003969999961555004 MOLE;amine:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N, amount is: 0.00036100001307204366 MOLE,Reagents are Base:CCC(C)(C)[O-].[Na+], amount is: 0.0007210000185295939 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.00016199999663513154 MOLE;metal and ligand:[Pd], amount is: 0.00010800000018207356 MOLE.Products are 0:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The aim of the reaction is test/optimization: 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (100 mg, 0.36 mmol), 4-(4-bromo-3-fluorobenzyl)morpholine (109 mg, 0.40 mmol), Palladium, 10% On Charcoal (115 mg, 0.11 mmol), racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (101 mg, 0.16 mmol) and Sodium tert-pentoxide (79 mg, 0.72 mmol) were dissolved in toluene (1.5 mL) and heated to 110 °C under argon. The reaction was monitorred by HPLC. After 16 h 81 % conversion was achieved. The reaction was stopped and the mixture was discarded. |
Here is a chemical reaction formula: Reactants are amine:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N, amount is: 0.00036100001307204366 MOLE;aryl halide:C1COCCN1CC2=CC(=C(C=C2)Br)F, amount is: 0.0003969999961555004 MOLE,Reagents are Base:CCC(C)(C)[O-].[Na+], amount is: 0.0007210000185295939 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C, amount is: 0.00016199999663513154 MOLE;metal and ligand:[Pd], amount is: 0.00010800000018207356 MOLE.Products are 0:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The aim of the reaction is test/optimization: 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (100 mg, 0.36 mmol), 4-(4-bromo-3-fluorobenzyl)morpholine (109 mg, 0.40 mmol), Palladium, 10% On Charcoal (115 mg, 0.11 mmol), Tri-o-tolylphosphine (49.4 mg, 0.16 mmol) and Sodium tert-pentoxide (79 mg, 0.72 mmol) were dissolved in toluene (1.5 mL) and heated to 110 °C under argon. The reaction was monitorred by HPLC. After 16 h 88 % conversion was achieved. The reaction was stopped and the mixture was discarded. |
Here is a chemical reaction formula: Reactants are amine:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N, amount is: 0.00036100001307204366 MOLE;aryl halide:C1COCCN1CC2=CC(=C(C=C2)Br)F, amount is: 0.0003969999961555004 MOLE,Reagents are Base:CCC(C)(C)[O-].[Na+], amount is: 0.0007210000185295939 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3, amount is: 0.00016199999663513154 MOLE;metal and ligand:[Pd], amount is: 0.00010800000018207356 MOLE.Products are 0:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The aim of the reaction is test/optimization: 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (100 mg, 0.36 mmol), 4-(4-bromo-3-fluorobenzyl)morpholine (109 mg, 0.40 mmol), Palladium, 10% On Charcoal (115 mg, 0.11 mmol), Triphenylphosphine (0.038 mL, 0.16 mmol) and Sodium tert-pentoxide (79 mg, 0.72 mmol) were dissolved in toluene (1.5 mL) and heated to 110 °C under argon. The reaction was monitorred by HPLC. After 16 h 73 % conversion was achieved. The reaction was stopped and the mixture was discarded. |
Here is a chemical reaction formula: Reactants are amine:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N, amount is: 0.00036100001307204366 MOLE;aryl halide:C1COCCN1CC2=CC(=C(C=C2)Br)F, amount is: 0.0003969999961555004 MOLE,Reagents are Base:CCC(C)(C)[O-].[Na+], amount is: 0.0007210000185295939 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 0.00016199999663513154 MOLE;metal and ligand:[Pd], amount is: 0.00016199999663513154 MOLE.Products are 0:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The aim of the reaction is test/optimization: 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (100 mg, 0.36 mmol), 4-(4-bromo-3-fluorobenzyl)morpholine (109 mg, 0.40 mmol), Palladium, 10% On Charcoal (115 mg, 0.11 mmol), (R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine (91 mg, 0.16 mmol) and Sodium tert-pentoxide (79 mg, 0.72 mmol) were dissolved in toluene (1.5 mL) and heated to 110 °C under argon. The reaction was monitorred by HPLC. After 16 h 79 % conversion was achieved. The reaction was stopped and the mixture was discarded. |
Here is a chemical reaction formula: Reactants are amine:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N, amount is: 0.00036100001307204366 MOLE;aryl halide:C1COCCN1CC2=CC(=C(C=C2)Br)F, amount is: 0.0003969999961555004 MOLE,Reagents are Base:CCC(C)(C)[O-].[Na+], amount is: 0.0007210000185295939 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.00016199999663513154 MOLE;metal and ligand:[Pd], amount is: 0.00010800000018207356 MOLE.Products are 0:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The aim of the reaction is test/optimization: 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (100 mg, 0.36 mmol), 4-(4-bromo-3-fluorobenzyl)morpholine (109 mg, 0.40 mmol), Palladium, 10% On Charcoal (115 mg, 0.11 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (94 mg, 0.16 mmol) and Sodium tert-pentoxide (79 mg, 0.72 mmol) were dissolved in toluene (1.5 mL) and heated to 110 °C under argon. The reaction was monitorred by HPLC. After 16 h 85 % conversion was achieved. The reaction was stopped and the mixture was discarded. |
Here is a chemical reaction formula: Reactants are amine:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N, amount is: 0.00036100001307204366 MOLE;aryl halide:C1COCCN1CC2=CC(=C(C=C2)Br)F, amount is: 0.0003969999961555004 MOLE,Reagents are Base:CCC(C)(C)[O-].[Na+], amount is: 0.0007210000185295939 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4, amount is: 0.00016199999663513154 MOLE;metal and ligand:[Pd], amount is: 0.00010800000018207356 MOLE.Products are 0:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The aim of the reaction is test/optimization: 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (100 mg, 0.36 mmol), 4-(4-bromo-3-fluorobenzyl)morpholine (109 mg, 0.40 mmol), Palladium, 10% On Charcoal (115 mg, 0.11 mmol), 2-Dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl (66.6 mg, 0.16 mmol) and Sodium tert-pentoxide (79 mg, 0.72 mmol) were dissolved in toluene (1.5 mL) and heated to 110 °C under argon. The reaction was monitorred by HPLC. After 16 h 85 % conversion was achieved. The reaction was stopped and the mixture was discarded. |
Here is a chemical reaction formula: Reactants are amine:C1OC2=C(O1)C(=C(C=C2)Cl)N, amount is: 0.005830000154674053 MOLE;aryl halide:CC(=O)NC1=NC=CC(=C1)Cl, amount is: 0.005830000154674053 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.011699999682605267 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.0006990000256337225 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.000291000003926456 MOLE.Products are 0:CC(=O)NC1=NC=CC(=C1)NC2=C(C=CC3=C2OCO3)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Reaction carried out in two batches in 20 ml microwave tubes. 5-chlorobenzo[d][1,3]dioxol-4-amine (1 g, 5.83 mmol), N-(4-chloropyridin-2-yl)acetamide (0.994 g, 5.83 mmol), XANTPHOS (0.405 g, 0.70 mmol), PALLADIUM(II) ACETATE (0.065 g, 0.29 mmol) and CESIUM CARBONATE (3.80 g, 11.66 mmol) were suspended in 2x DMA (12mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 30 minutes in the microwave reactor and cooled to RT. LC/MS showed completion. The reaction mixture was concentrated and diluted with EtOAc , and washed sequentially with water and saturated brine. The organic layer was dried over MgSO4, filtered and evaporated. The crude oil was triturated with EtOAc, Et2O and hexane to give a solid which was collected by filtration and dried under vacuum to give P1 N-(4-(5-chlorobenzo[d][1,3]dioxol-4-ylamino)pyridin-2-yl)acetamide (680mg, 38%)as a tan solid. NMR of this product showed product plus some DMA and aromatic impurities. The filtrate from the the above was concentrated and triturated again to give P2 N-(4-(5-chlorobenzo[d][1,3]dioxol-4-ylamino)pyridin-2-yl)acetamide (800mg, 45%) as a pale orange solid. NMR of this product showed it to be much cleaner than P1. |
Here is a chemical reaction formula: Reactants are amine:CN1CCC2=C(C1=O)C(=CC=C2)N, amount is: 0.018300000578165054 MOLE;aryl halide:C1=C(C(=CN=C1Cl)Cl)I, amount is: 0.018300000578165054 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.027400000020861626 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.001829999964684248 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.0009130000253207982 MOLE.Products are 0:CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: diacetoxypalladium (0.205 g, 0.91 mmol) was added to a stirred suspension of 2,5-dichloro-4-iodopyridine (5 g, 18.26 mmol), 8-amino-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (3.22 g, 18.26 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (1.056 g, 1.83 mmol) and cesium carbonate (8.92 g, 27.38 mmol) dissolved in 1,4-dioxane (100 mL). The resulting suspension was degassed (3 times) with nitrogen and was stirred at 100°C for 16 hours. The reaction mixture was allowed to cool to room temperature, diluted with DCM (100 mL) and filtered. The residue was washed with DCM. The filtrates was combined evaporated to dryness. The crude product was purified by flash chromatography on silica gel eluting with 0 to 10% ethyl acetate in dichloromethane. The solvent was evaporated to dryness to afford 8-(2,5-dichloropyridin-4-ylamino)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (2.500 g, 42.5 %) as a pale yellow solid. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=C(C(=CN=C1Cl)Cl)I, amount is: 0.0021899999119341373 MOLE;amine:CN1CCC2=C(C1=O)C(=CC=C2)N, amount is: 0.0021899999119341373 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.003289999905973673 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.00021899999410379678 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.00011000000085914508 MOLE.Products are 0:CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: diacetoxypalladium (24.59 mg, 0.11 mmol) was added to a stirred suspension of 2,5-dichloro-4-iodopyridine (600 mg, 2.19 mmol), 8-amino-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (386 mg, 2.19 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (127 mg, 0.22 mmol) and cesium carbonate (1071 mg, 3.29 mmol) in 1,4-dioxane (10 mL). The resulting suspension was degassed with nitrogen and was stirred at 100 °C for 18 hours. Reaction was allowed to cool to room temperature, quenched with water and extracted with EtOAc. Combined organic phases were washed with water, brine, dried over MgSO4 and concentrated to dryness. The crude product was purified by flash chromatography on silica gel eluting with 0 to 10% ethyl acetate in dichloromethane. The solvent was evaporated to dryness to afford 8-(2,5-dichloropyridin-4-ylamino)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (447 mg, 63.3 %) as a pale yellow crystalline solid. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=C(C(=CN=C1Cl)Cl)I, amount is: 0.01360000018030405 MOLE;amine:CN1CCC2=C(C1=O)C(=CC=C2)N, amount is: 0.01360000018030405 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0203000009059906 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.0013599999947473407 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.0006779999821446836 MOLE.Products are 0:CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: diacetoxypalladium (0.152 g, 0.68 mmol) was added to a stirred suspension of 2,5-dichloro-4-iodopyridine (3.71 g, 13.56 mmol), 8-amino-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (2.39 g, 13.56 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.785 g, 1.36 mmol) and cesium carbonate (6.63 g, 20.34 mmol) in 1,4-dioxane (70 mL). The resulting suspension was degassed with nitrogen and was stirred at 100 °C for 18 hours. Reaction was allowed to cool to room temperature, quenched with water (100 mL) and extracted with EtOAc*. Combined organic phases were washed with water, brine, dried over MgSO4 and concentrated to dryness. The crude product was purified by flash chromatography* on silica gel eluting with 0 to 10% ethyl acetate in dichloromethane. The solvent was evaporated to dryness to afford 8-(2,5-dichloropyridin-4-ylamino)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (2.160 g, 49.4 %) as a yellow crystalline solid. |
Here is a chemical reaction formula: Reactants are amine:CN1CCC2=C(C1=O)C(=CC=C2)N, amount is: 0.051100000739097595 MOLE;aryl halide:C1=C(C(=CN=C1Cl)Cl)I, amount is: 0.051100000739097595 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.07660000026226044 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.005109999794512987 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.0025500000920146704 MOLE.Products are 0:CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: diacetoxypalladium (0.573 g, 2.55 mmol) was added to a stirred suspension of 2,5-dichloro-4-iodopyridine (13.99 g, 51.07 mmol), 8-amino-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (9 g, 51.07 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (2.96 g, 5.11 mmol) and cesium carbonate (24.96 g, 76.61 mmol) dissolved in 1,4-dioxane (300 mL). The resulting suspension was degassed (3 times) with nitrogen and was stirred at 100°C for 16 hours. The reaction mixture was allowed to cool to room temperature, diluted with DCM (100 mL) and filtered. The residue was washed with DCM. The filtrates was combined and evaporated to dryness. The crude product was purified by flash chromatography on silica gel eluting with 0 to 10% ethyl acetate in dichloromethane. The solvent was evaporated to dryness to afford 8-(2,5-dichloropyridin-4-ylamino)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (9.80 g, 59.6 %) as a clear white solid. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=C(C(=CN=C1Cl)Cl)I, amount is: 0.27399998903274536 MOLE;amine:CONC(=O)C1=CC=CC=C1N, amount is: 0.2879999876022339 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.32899999618530273 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.020500000566244125 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.013700000010430813 MOLE.Products are 0:CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2,5-dichloro-4-iodopyridine (75 g, 273.84 mmol), 2-amino-N-methoxybenzamide (47.8 g, 287.53 mmol), cesium carbonate (107 g, 328.60 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (11.88 g, 20.54 mmol) were suspended in 1,4-dioxane (913 ml). Nitrogen was bubbled through the mixture for 20 minutes then diacetoxypalladium (3.07 g, 13.69 mmol) was added. Reaction was heated to reflux overnight under nitrogen. Reaction was allowed to cool to ~50°C and filtered. Filtered cake was washed with hot EtOH (2x300 mL) _._ Filtrate was concentrated to dryness to afford crude as a black solid (57 g). Filtered cake was re-washed with CH2Cl2/MeOH 9/1 (3x300 mL). Filtrate was combined with previous crude and concentrated to dryness to afford crude as a black solid (93 g). Crude was stirred in boiling EtOH (380 mL). Insoluble was filtered => _seemed to contain expected product / instantaneous cristallisation occured in the filtrate_. Flask was left standing overnight. Resulting crystals were filtered, washed with Et2O (x2) and dried to afford 2-(2,5-dichloropyridin-4-ylamino)-N-methoxybenzamide (33.4 g, 39.1%, EN03787-93-02) as a dark grey crystalline solid => _product crystallised with 1eq of EtOH._ Insoluble material was washed with EtOH, CH2Cl2 and dried overnight to afford 2-(2,5-dichloropyridin-4-ylamino)-N-methoxybenzamide (26.6 g, EN03787-93-01) => _not fully soluble in DMSO, seemed contaminated by minerals._ It was suspended in H2O (200 mL) and stirred at room temperature for 20 minutes. It was filtered, washed with EtOH (x2) and dried to afford an orange solid (3.8 g !!) => _not soluble in DMSO, probably only a few expected product in it !!_ |
Here is a chemical reaction formula: Reactants are aryl halide:C1=C(C(=CN=C1Cl)Cl)I, amount is: 0.03799999877810478 MOLE;amine:CONC(=O)C1=CC=CC=C1N, amount is: 0.039900001138448715 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.04560000076889992 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.002850000048056245 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.0019000000320374966 MOLE.Products are 0:CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2,5-dichloro-4-iodopyridine (10.4 g, 37.97 mmol), 2-amino-N-methoxybenzamide (6.63 g, 39.87 mmol), cesium carbonate (14.85 g, 45.57 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (1.648 g, 2.85 mmol) were suspended in 1,4-dioxane (130 mL). Nitrogen was bubbled through the mixture for 10 minutes then diacetoxypalladium (0.426 g, 1.90 mmol) was added. Flask was purged with nitrogen 3 times and heated to reflux for 16 hours. Reaction was allowed to cool to room temperature and diluted with CH2Cl2 (100 mL) (=> _trouble_ ) + MeOH (10 mL). Mixture was filtered _(filtrate is clear)_ and washed with CH2Cl2/MeOH 9/1 (2x100 mL) => _filtrate became troubled._ Filtrate was concentrated to dryness to afford crude as a dark brown solid (17.5 g). Filtered cake seemed to contain some product. It was suspended in H2O (200 mL) and stirred for 20 minutes. It was then filtered ( _long and tricky filtration !!_ ). Solid was dissolved in CH2Cl2/MeOH ( _big volume compare to the amount of solid !! it's quite insoluble_ ), dried over MgSO4 and concentrated to dryness to afford crude product (0.5 g...) as a dark green solid. Solids were combined (18 g) and recristallised from EtOH (85 mL). Flask was left standing over the weekend. Resulting crystals were filtered, washed with Et2O and dried to afford 2-(2,5-dichloropyridin-4-ylamino)-N-methoxybenzamide (8.20 g, 69.2 %) as a dark yellow crystalline solid => _product crystallised with 1eq of EtOH._ Filtrate was concentrated. Residue (7.7 g) was recristallised from EtOH (30 mL). Hot solution was seeded with crystals, from 1st batch, and flask was left standing overnight. Resulting crystals were filtered, washed with Et2O and dried to afford a dark yellow crystalline solid (1.68 g, EN03787-82-02) => _impure material (see UPLCMS & 1H NMR 03787-82-02)_ |
Here is a chemical reaction formula: Reactants are aryl halide:C1=C(C(=CN=C1Cl)Cl)I, amount is: 0.0007300000288523734 MOLE;amine:CNC(=O)C1=CC=CC=C1N, amount is: 0.0007300000288523734 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0010999999940395355 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 7.300000288523734e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 3.650000144261867e-05 MOLE.Products are 0:CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-amino-N-methylbenzamide (110 mg, 0.73 mmol), 2,5-dichloro-4-iodopyridine (200 mg, 0.73 mmol), diacetoxypalladium (8.20 mg, 0.04 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (42.3 mg, 0.07 mmol) and cesium carbonate (357 mg, 1.10 mmol) suspended in 1,4-dioxane (4 mL) was weighed out in a microwave vial and sealed. argon was let to bubble into the mixture for 5 minutes at rt then the resulting mixture was stirred at 100 °C for 1 hour. The reaction mixture was allowed to cool to room temperature under stirring and diluted with dichloromethane. Insolubles were removed by filtration and the filtrate was concentrated. The residue was triturated in DCM, collected by filtration and dried to afford 2-(2,5-dichloropyridin-4-ylamino)-N-methylbenzamide (150 mg, 69.4 %) as a off- white solid. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=C(C(=CN=C1Cl)Cl)I, amount is: 0.010999999940395355 MOLE;amine:CNC(=O)C1=CC=CC=C1N, amount is: 0.010999999940395355 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.021900000050663948 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.0006569999968633056 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.00043799998820759356 MOLE.Products are 0:CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Palladium(II) acetate (0.098 g, 0.44 mmol) was added to 2,5-dichloro-4-iodopyridine (3 g, 10.95 mmol), 2-amino-N-methylbenzamide (1.645 g, 10.95 mmol), Cesium carbonate (7.14 g, 21.91 mmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (0.380 g, 0.66 mmol) in dioxane (150 mL) under nitrogen. The resulting suspension was stirred at 80 °C for 18 hours. The reaction mixture was filtered and the filtrate was evaporated to dryness. The crude residue was triturated with DCM to give a solid which was collected by filtration and dried under vacuum to give 2-(2,5-dichloropyridin-4-ylamino)-N-methylbenzamide (1.58 g, 49 %) as a tan solid, LCMS indicated 87% pure. This was purified by flash silica chromatography, elution gradient 0 to 5% MeOH in DCM. Pure fractions were evaporated to dryness to afford 2-(2,5-dichloropyridin-4-ylamino)-N-methylbenzamide (1.040 g, 32.1 %) as a yellow solid. |
Here is a chemical reaction formula: Reactants are aryl halide:C1COCCN1CC2=CC(=C(C=C2)Cl)F, amount is: 0.0013899999903514981 MOLE;amine:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N, amount is: 0.0013899999903514981 MOLE,Reagents are Base:CC(C)(C)[O-].[K+], amount is: 0.0018100000452250242 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C, amount is: 0.0004199999966658652 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.00013899999612476677 MOLE.Products are 0:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To degassed 1,4-dioxane (13.900 ml) in a flame-dried and argonflushed 50 mL roundbottomed flask were added 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (386 mg, 1.39 mmol) and 4-(4-chloro-3-fluorobenzyl)morpholine (320 mg, 1.39 mmol) followed by POTASSIUM TERT-BUTOXIDE (203 mg, 1.81 mmol) whilst stirring. The resulting slurry was flushed with argon followed by addition of TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (128 mg, 0.14 mmol) and 2-Dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl (200 mg, 0.42 mmol), whereafter the dark violet reaction mixture was again flushed with argon and heated to 102 °C and stirred under argon for 15 h. The completion of the reaction was controlled by HPLC and the crude mixture was cooled to ambient temperatuer and then filtrated through Celite and washed through with dichloromethane. The solution was concentrated in vacuo and dissolved in a minimum amount of DMSO and purified via Preparative HPLC. The pooled fractions were concentrated in vacuo and added HCl. 5-fluoro-N-(2-fluoro-4-(morpholinomethyl)phenyl)-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (60.0 mg, 9.15 %) |
Here is a chemical reaction formula: Reactants are aryl halide:C1COCCN1CC2=CC(=C(C=C2)Cl)F, amount is: 0.003920000046491623 MOLE;amine:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N, amount is: 0.0038799999747425318 MOLE,Reagents are Base:CC(C)(C)[O-].[K+], amount is: 0.005090000107884407 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C, amount is: 0.000783999974373728 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.000391999987186864 MOLE.Products are 0:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To degassed 1,4-dioxane (39.2 ml) in a flame-dried and argonflushed 250 mL roundbottomed flask were added 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (1.076 g, 3.88 mmol) and 4-(4-chloro-3-fluorobenzyl)morpholine (0.9 g, 3.92 mmol) followed by POTASSIUM TERT-BUTOXIDE (0.572 g, 5.09 mmol) whilst stirring. The resulting slurry was flushed with argon and stirred for 5-10 minutes followed by addition of TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.359 g, 0.39 mmol) and 2-Dicyclohexylphosphino-2',4',6'-tri-iso- propyl-1,1'-biphenyl (0.374 g, 0.78 mmol), whereafter the reaction mixture was flushed with argon again and heated to 102 °C and stirred under argon for 3 h. No further conversion occurred after 2 hours. The completion of the reaction was controlled by HPLC and the crude mixture was cooled to ambient temperatuer and then filtrated through Celite and washed through with dichloromethane. The solution was concentrated in vacuo and dissolved in 14 ml dichloromethane and purified by ISCO and then by prep-HPLC. The pooled fractions were concentrated in vacuo and added HCl to give 5-fluoro-N-(2-fluoro-4-(morpholinomethyl)phenyl)-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (0.227 g, 11.43 %) |
Here is a chemical reaction formula: Reactants are aryl halide:C[C@@H](C1=NC=C(C=N1)F)NC2=NC(=NC(=N2)Cl)N3CCOCC3, amount is: 0.00029399999766610563 MOLE;amine:CC1=CN=C(S1)N, amount is: 0.00044100001105107367 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0007360000163316727 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 2.9400000130408444e-05 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 1.4700000065204222e-05 MOLE.Products are 0:CC1=CN=C(S1)NC2=NC(=NC(=N2)N3CCOCC3)N[C@@H](C)C4=NC=C(C=N4)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (S)-4-chloro-N-(1-(5-fluoropyrimidin-2-yl)ethyl)-6-morpholino-1,3,5-triazin-2-amine (100 mg, 0.29 mmol), 5-methylthiazol-2-amine (50.4 mg, 0.44 mmol), BINAP (18.33 mg, 0.03 mmol), Pd2(dba)3 (13.48 mg, 0.01 mmol) and Cs2CO3 (240 mg, 0.74 mmol) were combined in a microwave reaction tube and vacuum purged. The tube was then charged with nitrogen and dioxane (0.589 mL) was added. The tube was then evacuated again and placed under a nitrogen balloon for 8 hours. LC/MS confirmed formation of the product (m+1 = 418) at t= 2.07 min. The reaction mixture was concentrated in vacuo leaing a brown solid (472 mg). This material was the redissolved in EtOAc, filtered through Celite, washed with water and dried with Na2SO4. Concentration in vacuo gave a rust solid (272 mg). This material was purified by ISCO (0-10% MeOH/DCM). Concentration of the fractions in vacuo gave an orange oil. This material was then repurifed by ISCO (4-8% MeOH/DCM) and (0-4% MeOH/DCM). Both gradients resulted in impure material, so the recovered orange oil was purified again by ISCO (60-100% EtOAc/Hex). Concentration in vacuo gave a yellow solid (34.8 mg). LC/MS showed this material to still be only 80% pure, so it was purified again by ISCO (55-95% EtOAc/Hex). A yellow solid (25.4 mg) was again collected. Although LC/MS and HPLC showed this material to be only ~80% pure, the NMR confirmed this material to be the desired product, (S)-N2-(1-(5-fluoropyrimidin-2-yl)ethyl)-N4-(5-methylthiazol-2-yl)-6-morpholino-1,3,5-triazine-2,4-diamine, with 95% purity. 1H NMR (300 MHz, CHLOROFORM- _d_ ) d ppm 11.87 (br. s., 1 H) 9.48 (br. s., 1 H) 8.58 (s, 2 H) 7.01 (s, 1 H) 5.35 (t, 1 H) 3.28 - 4.23 (m, 8 H) 2.38 (s, 3 H) 1.59 (d, 4 H) |
Here is a chemical reaction formula: Reactants are amine:CC1=NN(C=C1N)C, amount is: 0.00139999995008111 MOLE;aryl halide:CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C#N)Cl, amount is: 0.0006980000180192292 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 8.369999704882503e-05 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 8.369999704882503e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 5.579999924520962e-05 MOLE.Products are 0:CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NC)C#N)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(2-chloro-5-cyanopyridin-4-ylamino)-N-methylbenzamide (200 mg, 0.70 mmol), Palladium(II) acetate (12.53 mg, 0.06 mmol), 1,3-dimethyl-1H-pyrazol-4-amine (155 mg, 1.40 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (48.4 mg, 0.08 mmol) and Cesium carbonate (273 mg, 0.84 mmol) were suspended in dioxane (5 mL) into a test tube. The reaction was purged for 5 mins with nitrogen and then heated to 90 °C for 24 hours with stirring. The reaction was cooled to cooled to RT. The crude product was purified by ion exchange chromatography, using an SCX column. The desired crude product was eluted from the column using 7M NH3/MeOH and fractions were evaporated to dryness to afford crude product .The crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5µ silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford 2-(5-cyano-2-(1,3-dimethyl-1H-pyrazol-4-ylamino)pyridin-4-ylamino)-N-methylbenzamide (126 mg, 50.0 %) as a beige solid. |
Here is a chemical reaction formula: Reactants are amine:CN1C(=CC(=N1)OC)N, amount is: 0.0006980000180192292 MOLE;aryl halide:CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C#N)Cl, amount is: 0.0003490000090096146 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 4.189999890513718e-05 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 4.189999890513718e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 2.789999962260481e-05 MOLE.Products are 0:CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C#N)NC3=CC(=NN3C)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(2-chloro-5-cyanopyridin-4-ylamino)-N-methylbenzamide (100 mg, 0.35 mmol), Palladium(II) acetate (6.26 mg, 0.03 mmol), [Reactants], 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (24.22 mg, 0.04 mmol) and Cesium carbonate (136 mg, 0.42 mmol) were suspended in dioxane (3 mL) into a test tube. The reaction was purged for 5 mins with nitrogen and then heated to 90 °C for 18 hours with stirring. The reaction was cooled to cooled to RT. The crude product was purified by ion exchange chromatography, using an SCX column. The desired crude product was eluted from the column using 7M NH3/MeOH and fractions were evaporated to dryness to afford crude product .The crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5µ silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford 2-(5-cyano-2-(3-methoxy-1-methyl-1H-pyrazol-5-ylamino)pyridin-4-ylamino)-N-methylbenzamide (72.0 mg, 54.7 %) as a beige solid. |
Here is a chemical reaction formula: Reactants are amine:CC1=NN(C=C1N)C, amount is: 0.003800000064074993 MOLE;aryl halide:CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3C#N)Cl, amount is: 0.0019000000320374966 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0002280000044265762 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.0002280000044265762 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.00015199999324977398 MOLE.Products are 0:CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC4=C3C(=O)N(CC4)C)C#N)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 6-chloro-4-(2-methyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-8-ylamino)nicotinonitrile (595 mg, 1.90 mmol), Palladium(II) acetate (34.2 mg, 0.15 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (132 mg, 0.23 mmol), 1,3-dimethyl-1H-pyrazol-4-amine (423 mg, 3.80 mmol) and Cesium carbonate (744 mg, 2.28 mmol) were suspended in dioxane (40 mL). The reaction was purged for 5 mins with nitrogen and then heated to 90 °C for 2 hour with stirring. The reaction was cooled to RT. The crude product was purified by ion exchange chromatography, using an SCX column. The desired crude product was eluted from the column using 7M NH3/MeOH and fractions were evaporated to dryness to afford crude product .The crude product was purified by preparative basic HPLC. Fractions containing the desired compound were evaporated to dryness to afford 6-(1,3-dimethyl-1H-pyrazol-4-ylamino)-4-(2-methyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-8-ylamino)nicotinonitrile (54.0 mg, 7.33 %) as a beige solid. |
Here is a chemical reaction formula: Reactants are aryl halide:CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3C#N)Cl, amount is: 0.00015999999595806003 MOLE;amine:CC1=NN(C=C1N)C, amount is: 0.00031999999191612005 MOLE,Reagents are Base:C1=CC=C(C=C1)[O-].[Na+], amount is: 0.00015999999595806003 MOLE,Solvents are Solvent:COCCOC, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 1.9999999494757503e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 1.2800000149582047e-05 MOLE.Products are 0:CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC4=C3C(=O)N(CC4)C)C#N)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1,3-dimethyl-1H-pyrazol-4-amine (35.5 mg, 0.32 mmol), 6-chloro-4-(2-methyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-8-ylamino)nicotinonitrile (50 mg, 0.16 mmol)sodium phenolate (18.56 mg, 0.16 mmol),(R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T- BUTYLPHOSPHINE (8.74 mg, 0.02 mmol) and diacetoxypalladium (2.87 mg, 0.01 mmol) were suspended in DME (1 mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 30 minutes in the microwave reactor and cooled to RT. LCMS indicated 47% product, ~8% dimer, ~8% hydrolysed Starting material , Starting material 25% and an unknown 17% @ 2.66 and unknown 12% @ 0.77. Sample combined with en01521-027 and en01521-034, SCX'd and sent to purification group. The crude product was purified by preparative basic HPLC. Fractions containing the desired compound were evaporated to dryness to afford 6-(1,3-dimethyl-1H-pyrazol-4-ylamino)-4-(2-methyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-8-ylamino)nicotinonitrile (34.0 mg, 54.9 %) as a brown solid. |
Here is a chemical reaction formula: Reactants are aryl halide:CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3C#N)Cl, amount is: 0.0015999999595806003 MOLE;amine:CC1=NN(C=C1N)C, amount is: 0.0031900000758469105 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0019199999514967203 MOLE,Solvents are Solvent:COCCOC, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 0.00015999999595806003 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.00015999999595806003 MOLE.Products are 0:CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC4=C3C(=O)N(CC4)C)C#N)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1,3-dimethyl-1H-pyrazol-4-amine (355 mg, 3.19 mmol), 6-chloro-4-(2-methyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-8-ylamino)nicotinonitrile (500 mg, 1.60 mmol), Cesium carbonate (625 mg, 1.92 mmol), Palladium(II) acetate (28.7 mg, 0.13 mmol)and (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (87 mg, 0.16 mmol) were suspended in DME (10 mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 30 minutes in the microwave reactor and cooled to RT. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and pure fractions were evaporated to dryness. The crude product was handed to the purification group and purified by basic preparative HPLC. Fractions containing the desired compound were evaporated to dryness to afford 6-(1,3-dimethyl-1H-pyrazol-4-ylamino)-4-(2-methyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-8-ylamino)nicotinonitrile (271 mg, 43.8 %) as a brown solid. |
Here is a chemical reaction formula: Reactants are amine:CC1=NN(C=C1N)C, amount is: 0.0031999999191612005 MOLE;aryl halide:CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3C#N)Cl, amount is: 0.0015999999595806003 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0019199999514967203 MOLE,Solvents are Solvent:COCCOC, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 0.00015999999595806003 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.00015999999595806003 MOLE.Products are 0:CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC4=C3C(=O)N(CC4)C)C#N)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 6-chloro-4-(2-methyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-8-ylamino)nicotinonitrile (500 mg, 1.60 mmol), 1,3-Dimethyl-1H-pyrazol-4-ylamine (355 mg, 3.20 mmol) and Cesium carbonate (625 mg, 1.92 mmol), Palladium(II) acetate (28.7 mg, 0.13 mmol) and (R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t- butylphosphine (90 mg, 0.16 mmol) were suspended in DME (10 mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 30 minutes in the microwave reactor and cooled to RT. This was combined with reactions EN01370-84-87 and concentrated. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. Mixed fractions were combined and re-columned. This prcess was repeated a further 3 times! 'Pure' fractions were combined and evaporated to dryness to afford 6-(1,3-dimethyl-1H-pyrazol-4-ylamino)-4-(2-methyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-8-ylamino)nicotinonitrile (484 mg, 15.63 %) as a yellow solid (1.08g) - 100% by LCMS and clean by TLC but the NMR is not great. Passed onto the purification group.The crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5µ silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford the required product. 200mg trial purification - resulted in 137mg pure - EN01370-88-1 Rest of the material processed to give EN01370-88-2 (347mg and 177mg) |
Here is a chemical reaction formula: Reactants are aryl halide:C1OC2=C(C(=CN=C2O1)Cl)N, amount is: 0.0006099999882280827 MOLE;amine:C1CC1C(=O)NC2=NC=CC(=C2)Cl, amount is: 0.0005089999758638442 MOLE,Reagents are Base:C1CCC2=NCCCN2CC1, amount is: 5.089999831398018e-05 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 5.089999831398018e-05 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd], amount is: 4.579999949783087e-05 MOLE.Products are 0:C1CC1C(=O)NC2=NC=CC(=C2)NC3=C4C(=NC=C3Cl)OCO4, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (0.190 mL, 1.27 mmol) was added to a mixture of N-(4-chloropyridin-2-yl)cyclopropanecarboxamide (100 mg, 0.51 mmol), 6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-amine (105 mg, 0.61 mmol) and BIS(DIBENZYLIDENEACETONE)PALLADIUM(0) (26.3 mg, 0.05 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (29.4 mg, 0.05 mmol) in toluene (1 mL) in a microwave tube. The reaction was degased, purged with argon and heated to 130 °C over a period of 7 hours in an oil bath. The mixture was diluted with dichloromethane, washed with water (emulsion), with brine, dried over MgSO4 and concentrated. The crude product was purified by flash chromatography on silica gel eluting with 0 to 3% methanol in dichloromethane. The solvent was evaporated to dryness to afford N-(4-(6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-ylamino)pyridin-2-yl)cyclopropanecarboxamide (55.0 mg, 32.5 %) as a yellow solid. |
Here is a chemical reaction formula: Reactants are amine:C1CC1C(=O)NC2=NC=CC(=C2)Cl, amount is: 0.0203000009059906 MOLE;aryl halide:C1OC2=C(C(=CN=C2O1)Cl)N, amount is: 0.0203000009059906 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.040699999779462814 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.0024399999529123306 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.001019999966956675 MOLE.Products are 0:C1CC1C(=O)NC2=NC=CC(=C2)NC3=C4C(=NC=C3Cl)OCO4, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: N-(4-chloropyridin-2-yl)cyclopropanecarboxamide (4 g, 20.34 mmol), 6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-amine (3.51 g, 20.34 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (1.412 g, 2.44 mmol), diacetoxypalladium (0.228 g, 1.02 mmol) and cesium carbonate (13.26 g, 40.68 mmol) were suspended in 1,4-dioxane (75 mL) and sealed into 5 microwave tubes. The reaction was heated to 150 °C for 30 minutes in the microwave reactor and cooled to RT. The reaction mixture was diluted with EtOAc (250 mL) and washed with water (250 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford and orange gum. The gum was dissolved in a little ether, then isohexane was added to precipitate N-(4-(6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-ylamino)pyridin-2-yl)cyclopropanecarboxamide (2.180 g, 32.2 %) as a white solid. |
Here is a chemical reaction formula: Reactants are aryl halide:C1OC2=C(C(=CN=C2O1)Cl)N, amount is: 0.0040699997916817665 MOLE;amine:C1CC1C(=O)NC2=NC=CC(=C2)Cl, amount is: 0.0040699997916817665 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.008139999583363533 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.0004879999905824661 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.00020300000323913991 MOLE.Products are 0:C1CC1C(=O)NC2=NC=CC(=C2)NC3=C4C(=NC=C3Cl)OCO4, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: N-(4-chloropyridin-2-yl)cyclopropanecarboxamide (0.8 g, 4.07 mmol), 6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-amine (0.702 g, 4.07 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.282 g, 0.49 mmol), diacetoxypalladium (0.046 g, 0.20 mmol) and cesium carbonate (2.65 g, 8.14 mmol) were suspended in 1,4-dioxane (15 mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 30 minutes in the microwave reactor and cooled to RT. The reaction mixture was evaporated and partitioned between EtOAc (50 mL) and water (50 mL). The mixture was filtered and the organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 5% MeOH in DCM. Pure fractions were evaporated to dryness to afford N-(4-(6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-ylamino)pyridin-2-yl)cyclopropanecarboxamide (0.384 g, 28.4 %) as a white solid. Impure fractions were combined and purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford more crude material. This material was triturated with DCM to afford a second batch of the material. |
Here is a chemical reaction formula: Reactants are amine:C1CC1C(=O)NC2=NC=CC(=C2)Cl, amount is: 0.005090000107884407 MOLE;aryl halide:C1OC2=C(C(=CN=C2O1)Cl)N, amount is: 0.005090000107884407 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.01269999984651804 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.0005590000073425472 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.00039999998989515007 MOLE.Products are 0:C1CC1C(=O)NC2=NC=CC(=C2)NC3=C4C(=NC=C3Cl)OCO4, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of N-(4-chloropyridin-2-yl)cyclopropanecarboxamide (1 g, 5.09 mmol), 6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-amine (0.878 g, 5.09 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.324 g, 0.56 mmol), diacetoxypalladium (0.090 g, 0.40 mmol), cesium carbonate (4.14 g, 12.71 mmol) and dioxane (18 mL) was degased, purged (x3) with argon and heated to reflux over a period of 4 hours in an oil bath (110°C). The reaction was complete. The reaction mixture was allowed to warm to room temperature diluted with water (25ml), a saturated solution of NH4Cl (35ml). Extraction with dichloromethane (x2), the organic was washed with a saturated aqueous solution of brine, dried over magnesium sulfate and concentrated. The crude product was purified by flash chromatography on silica gel eluting with 0 to 2% methanol in dichloromethane. The solvent was evaporated, the product was diluted in dichloromethane. The solution was filtered through PTFE filter 0.45µm, the filtrate was concentrated to dryness to afford N-(4-(6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-ylamino)pyridin-2-yl)cyclopropanecarboxamide (1.200 g, 70.9 %) as a white crystalline solid. |
Here is a chemical reaction formula: Reactants are aryl halide:C1OC2=C(C(=CN=C2O1)Cl)N, amount is: 0.0040699997916817665 MOLE;amine:C1CC1C(=O)NC2=NC=CC(=C2)Cl, amount is: 0.0040699997916817665 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.008139999583363533 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.0004879999905824661 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.00020300000323913991 MOLE.Products are 0:C1CC1C(=O)NC2=NC=CC(=C2)NC3=C4C(=NC=C3Cl)OCO4, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: N-(4-chloropyridin-2-yl)cyclopropanecarboxamide (0.8 g, 4.07 mmol), 6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-amine (0.702 g, 4.07 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.282 g, 0.49 mmol), diacetoxypalladium (0.046 g, 0.20 mmol) and cesium carbonate (2.65 g, 8.14 mmol) were suspended in 1,4-dioxane (15 mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 30 minutes in the microwave reactor and cooled to RT. The reaction mixture was diluted with EtOAc (50 mL) and washed with water (50 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford N-(4-(6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-ylamino)pyridin-2-yl)cyclopropanecarboxamide (0.592 g, 43.7 %) as a white solid. |
Here is a chemical reaction formula: Reactants are amine:CCN1CCNCC1, amount is: 0.007420000154525042 MOLE;aryl halide:C1COCCN1C2=CC(=O)C3=C(O2)C(=CC=C3)C4=C5C(=C(C=C4)I)C6=CC=CC=C6S5, amount is: 0.003710000077262521 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.007420000154525042 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.000742000003810972 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.000742000003810972 MOLE.Products are 0:CCN1CCN(CC1)C2=C3C4=CC=CC=C4SC3=C(C=C2)C5=CC=CC6=C5OC(=CC6=O)N7CCOCC7, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 8-(1-iododibenzo[b,d]thiophen-4-yl)-2-morpholino-4H-chromen-4-one (2 g, 3.71 mmol), 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL (0.462 g, 0.74 mmol), CESIUM CARBONATE (3.62 g, 11.12 mmol) and PALLADIUM (II) ACETATE (0.166 g, 0.74 mmol) were weighed out in a flask and inerted with argon. toluene (25 ml) and 1-ethylpiperazine (0.942 ml, 7.42 mmol) were added and the mixture was degassed several times with argon. The reaction was stirred at 110 °C (bath) for 2 hours. The reaction was incomplete. 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL (0.462 g, 0.74 mmol) and PALLADIUM (II) ACETATE (0.166 g, 0.74 mmol) were added, the reaction mixture was purged with argon, and the mixture was stirred at 110 °C for 5 hours. Reaction was quite clean: Crude LCMS showed very little de-iodo by-product and starting material left. The reaction was diluted with dichloromethane and insolubles were removed by filtration. The filtrate was concentrated to dryness. The crude product was purified by flash chromatography on silica gel eluting with 0 to 5% methanol in dichloromethane. The solvent was evaporated, the resulting solid was stirred in diethyl ether (40 ml) for 2 days. The product was filtered to give a solid which was collected by filtration and dried under vacuum to give 8-(1-(4-ethylpiperazin-1-yl)dibenzo[b,d]thiophen-4-yl)-2-morpholino-4H-chromen-4-one (0.950 g, 48.7 %) as a pale beige solid. Melting point: 221-224°C Purity check: 99%, Et2O: 0.06 mole/mole, H2O: 0.3 mole/mole H NMR strength: 97% +/- 3% |
Here is a chemical reaction formula: Reactants are amine:CCN1CCNCC1, amount is: 7.419999747071415e-05 MOLE;aryl halide:C1COCCN1C2=CC(=O)C3=C(O2)C(=CC=C3)C4=C5C(=C(C=C4)I)C6=CC=CC=C6S5, amount is: 3.7099998735357076e-05 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 5.560000136028975e-05 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 3.710000100909383e-06 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 9.269999736716272e-07 MOLE.Products are 0:CCN1CCN(CC1)C2=C3C4=CC=CC=C4SC3=C(C=C2)C5=CC=CC6=C5OC(=CC6=O)N7CCOCC7, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 8-(1-iododibenzo[b,d]thiophen-4-yl)-2-morpholino-4H-chromen-4-one (20 mg, 0.04 mmol), 1-ethylpiperazine (9.42 µl, 0.07 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (2.145 mg, 3.71 µmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM (0.849 mg, 0.93 µmol) and 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (16.62 µl, 0.11 mmol) were suspended in dioxane (250 µl) and sealed into a microwave tube. The reaction was degased, purged with argon and heated to 130 °C over a period of 45 minutes in the microwave reactor. No reaction. |
Here is a chemical reaction formula: Reactants are amine:CC(=O)N1CCNCC1, amount is: 0.1289999932050705 MOLE;aryl halide:COC1=C(C=C(C=C1)Br)[N+](=O)[O-], amount is: 0.1289999932050705 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.01549999974668026 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.01549999974668026 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.010300000198185444 MOLE.Products are 0:CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)OC)[N+](=O)[O-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-bromo-1-methoxy-2-nitrobenzene (30 g, 129.29 mmol), 1-(piperazin-1-yl)ethanone (16.57 g, 129.29 mmol), cesium carbonate (84 g, 258.59 mmol),diacetoxypalladium (2.322 g, 10.34 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (8.98 g, 15.52 mmol) in dioxane (200 mL) were degazed with nitrogen and stirred at 100°C for 1 hour. The reaction mixture was allowed to cool to room temperature, water (1000mL) was added and mixture was filtered on celite. The aq. layer was extracted with CH2Cl2 (2X500mL). The organic layer was dried on MgSO4, filtered and concentrated to dryness to afford the crude product. This product was purified by flash chromatography on silica gel eluting with ethyl acetate - methanol (92-8), the solvents were evaporated to dryness to afford 1-(4-(4-methoxy-3-nitrophenyl)piperazin-1-yl)ethanone (10.80 g, 29.9 %) |
Here is a chemical reaction formula: Reactants are amine:CC(=O)N1CCNCC1, amount is: 0.07760000228881836 MOLE;aryl halide:COC1=C(C=C(C=C1)Br)[N+](=O)[O-], amount is: 0.07760000228881836 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.009309999644756317 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.009309999644756317 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.006209999788552523 MOLE.Products are 0:CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)OC)[N+](=O)[O-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1-(piperazin-1-yl)ethanone (9.94 g, 77.58 mmol), Cesium carbonate (50.6 g, 155.15 mmol), XANTPHOS (5.39 g, 9.31 mmol) and Pd(OAc)2 (1.393 g, 6.21 mmol) were added to a stirred solution of 4-bromo-1-methoxy-2-nitrobenzene (18 g, 77.58 mmol) dissolved in dioxane (120 ml). The resulting suspension was heated to 120 °C (bath) over a period of 1 hour. The reaction mixture was allowed to cool and the residual cesium carbonate was removed by filtration through a pad of Dicalite speed plus, washing with dichloromethane. The solvent was removed under reduced pressure to give a dark oil. PBO-02628-53-01 w= 45 g The crude product in solution in DCM was added to a silica gel column and was eluted with methanol 0 to 20% in EtOAc (NOVASEP). Collected fractions to dryness to afford 1-(4-(4-methoxy-3-nitrophenyl)piperazin-1-yl)ethanone (17.96 g, 83 %) as a yellow solid. PBO-02628-53-02 |
Here is a chemical reaction formula: Reactants are amine:CC(=O)N1CCNCC1, amount is: 0.006459999829530716 MOLE;aryl halide:COC1=C(C=C(C=C1)Br)[N+](=O)[O-], amount is: 0.006459999829530716 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.000775999971665442 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.000775999971665442 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.0005169999785721302 MOLE.Products are 0:CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)OC)[N+](=O)[O-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-bromo-1-methoxy-2-nitrobenzene (1.5 g, 6.46 mmol), 1-(piperazin-1-yl)ethanone (0.829 g, 6.46 mmol), CESIUM CARBONATE (4.21 g, 12.93 mmol), XANTPHOS (0.449 g, 0.78 mmol) and PdOAc2 (0.116 g, 0.52 mmol) were suspended in dioxane (20 ml) and sealed into a microwave tube. The reaction was heated to 120 °C for 90 minutes in the microwave reactor and cooled to RT. The reaction mixture was filtered through celite with ethyl acetate (50 mL). The filtrate was evaporated to dryness. The crude product was purified by flash silica chromatography in EtOAc. Pure fractions were evaporated to dryness to afford 1-(4-(4-methoxy-3-nitrophenyl)piperazin-1-yl)ethanone (0.022 g, 1.218 %) as a brown solid. |
Here is a chemical reaction formula: Reactants are aryl halide:COC1=C(C=C(C=C1)Br)[N+](=O)[O-], amount is: 0.006459999829530716 MOLE;amine:CC(=O)N1CCNCC1, amount is: 0.006459999829530716 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.000775999971665442 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.000775999971665442 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.0005169999785721302 MOLE.Products are 0:CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)OC)[N+](=O)[O-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-bromo-1-methoxy-2-nitrobenzene (1.5 g, 6.46 mmol) was added in one portion to 1-(piperazin-1-yl)ethanone (0.829 g, 6.46 mmol), CESIUM CARBONATE (4.21 g, 12.93 mmol), XANTPHOS (0.449 g, 0.78 mmol) and PdOAc2 (0.116 g, 0.52 mmol) in dioxane (20 ml) under nitrogen. The resulting mixture was stirred at 120 °C for 3 hours. The reaction mixture was filtered through celite and the fitrate evaporated to dryness. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. Pure fractions were evaporated to dryness to afford 1-(4-(4-methoxy-3-nitrophenyl)piperazin-1-yl)ethanone (0.025 g, 1.385 %) as a brown oil. |
Here is a chemical reaction formula: Reactants are aryl halide:CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl, amount is: 0.0008009999874047935 MOLE;amine:CC1=NN(C=C1N)C, amount is: 0.0012000000569969416 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 9.609999688109383e-05 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 9.609999688109383e-05 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 6.410000059986487e-05 MOLE.Products are 0:CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(2,5-dichloropyridin-4-ylamino)-N-methoxybenzamide (250 mg, 0.80 mmol), 1,3-dimethyl-1H-pyrazol-4-amine (134 mg, 1.20 mmol), Sodium tert-butoxide (115 mg, 1.20 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (55.6 mg, 0.10 mmol) and BIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (58.7 mg, 0.06 mmol) were suspended in dioxane (15 mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 30 minutes in the microwave reactor and cooled to RT. Reaction not complete by LCMS so more 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (55.6 mg, 0.10 mmol), BIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (58.7 mg, 0.06 mmol) and 1,3-dimethyl-1H-pyrazol-4-amine (134 mg, 1.20 mmol) were added and the reaction heated to 150 ºC for a further 30 minutes in the microwave reactor and cooled to RT. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and pure fractions were evaporated to dryness to afford crude product as a tan gum. The sample was given to the purification group for purification by preparative HPLC. Fractions containing the desired compound were evaporated to dryness to afford 2-(5-chloro-2-(1,3-dimethyl-1H-pyrazol-4-ylamino)pyridin-4-ylamino)-N-methoxybenzamide (44.3 mg, 14.30 %) as a tan solid. |
Here is a chemical reaction formula: Reactants are amine:CC1CNCC(N1)C, amount is: 0.0002479999966453761 MOLE;aryl halide:COC1=C(C=CC(=C1)Br)NC2=NC=C(C(=N2)C3=CN=C4N3C=CC=C4)Cl, amount is: 0.0002479999966453761 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0024800000246614218 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 9.940000381902792e-06 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 4.970000190951396e-06 MOLE.Products are 0:CC1CN(CC(N1)C)C2=CC(=C(C=C2)NC3=NC=C(C(=N3)C4=CN=C5N4C=CC=C5)Cl)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: N-(4-bromo-2-methoxyphenyl)-5-chloro-4-(imidazo[1,2-a]pyridin-3-yl)pyrimidin-2-amine (107 mg, 0.25 mmol), 2,6-dimethylpiperazine (28.4 mg, 0.25 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (5.75 mg, 9.94 µmol), diacetoxypalladium (1.116 mg, 4.97 µmol) and cesium carbonate (162 mg, 0.50 mmol) were suspended in 1,4-dioxane (2 mL) . The reaction was purged with nitrogen and heated to 140 °C for 6 hours in an oil bath. Control LC/MS : no traces of expected product. |
Here is a chemical reaction formula: Reactants are aryl halide:CC1=CN=C(N=C1C2=CN(C3=CC=CC=C32)S(=O)(=O)C4=CC=CC=C4)Cl, amount is: 0.005210000090301037 MOLE;amine:CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)N)OC, amount is: 0.005210000090301037 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0005210000090301037 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.0005210000090301037 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.0002610000083222985 MOLE.Products are 0:CC1=CN=C(N=C1C2=CN(C3=CC=CC=C32)S(=O)(=O)C4=CC=CC=C4)NC5=C(C=C(C=C5)N6CCN(CC6)C(=O)C)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Cesium carbonate (2.55 g, 7.82 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.301 g, 0.52 mmol) and diacetoxypalladium (0.058 g, 0.26 mmol) were added to a stirred suspension of 3-(2-chloro-5-methylpyrimidin-4-yl)-1-(phenylsulfonyl)-1H-indole (2 g, 5.21 mmol) and 1-(4-(4-amino-3-methoxyphenyl)piperazin-1-yl)ethanone (1.299 g, 5.21 mmol) in 1,4-dioxane (50 ml). The resulting suspension was degassed with argon and stirred at 90 °C for 2 hours. After cooling, the mixture was filtered through a pad of Dicalite speed plus and washed with dichloromethane. The solvent were evaporated. PBO-01132-93-01 The crude product was purified by flash chromatography on silica gel (Merck cartrige SVP D40 - SI60 16-40µm - 90g) eluting with 0 up to 100% EtOAc in dichloromethane . The 1-(4-(3-methoxy-4-(5-methyl-4-(1-(phenylsulfonyl)-1H-indol-3-yl)pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone (1.760 g, 56.6 %) was obtained as a yellow oil. PBO-01132-93-02 An impure batch was obtained. PBO-01132-93-03 |
Here is a chemical reaction formula: Reactants are amine:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N, amount is: 0.00018400000408291817 MOLE;aryl halide:C1COCCN1CC2=CC=C(C=C2)Br, amount is: 0.0001990000018849969 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.00028899998869746923 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 8.809999599179719e-06 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 4.909999915980734e-06 MOLE.Products are 0:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=CC=C(C=C4)CN5CCOCC5, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The aim of the reaction is optimization. Tris(dibenzylideneacetone)dipalladium(0) (4.5 mg, 4.91 µmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (5.1 mg, 8.81 µmol) were dissolved in dioxane (1.8 mL) in a 10 mL Schlenk tube and activated at 100 °C for 6 min under argon. Then 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (51 mg, 0.18 mmol), 4-(4-bromobenzyl)morpholine (51 mg, 0.20 mmol) and Cesium carbonate (94 mg, 0.29 mmol) were added. It was degassed again and stirred at 100 °C under argon. The reaction was followed by HPLC. After 26 h 85.5 % conversion was obtained. 20 % by-product formation was detected. Finally, the reaction mixture was discarded. |
Here is a chemical reaction formula: Reactants are aryl halide:C1COCCN1CC2=CC=C(C=C2)Br, amount is: 0.03700000047683716 MOLE;amine:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N, amount is: 0.035999998450279236 MOLE,Reagents are Base:CCC(C)(C)[O-].[Na+], amount is: 0.0575999990105629 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.0006479999865405262 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.000539999979082495 MOLE.Products are 0:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=CC=C(C=C4)CN5CCOCC5, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Tris(dibenzylideneacetone)dipalladium(0) (0.494 g, 0.54 mmol) and9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (0.375 g, 0.65 mmol) were dissolved in toluene (160 mL) in a 1 L reactor equipped with a condensor and activated at 100 °C for 6 min under argon. Then 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (9.98 g, 36 mmol), 4-(4-bromobenzyl)morpholine (9.48 g, 37 mmol), Sodium tert- pentoxide (6.34 g, 57.60 mmol) and toluene (200 mL) were added. The reaction mixture became sticky yellowish green. It was stirred at 100 °C under argon. The reaction was followed by HPLC. After 3 h no conversion was obtained. The mixture was stirred overnight but the conversion did not move. Then the mixture was cooled to 50 ºC, Pd-complex (5 mol%) and Xantphos (6 mol%) as preactivated catalyst in toluene (100 ml) were added to the mixture, it was degassed carefully, then it was put under argon. Then the reaction mixture was heated at 100 ºC. After 1 h full conversion was detected. The reaction mixture was cooled to room temperature, diluted with dichloromethane (600 mL), extracted with water (4*500 mL), washed with brine (1*500 mL) and dried over Na2SO4. Filtration and concentration afforded orange brown solid. This solid was slurried in EtOAc ( 50 mL) and stirred at reflux point (78 °C) for 10 min. Then it was cooled to room temperature with stirring and filtered. The filtercake was washed with _n_ -pentane (80 mL). Orange filtercake was obtained which still had some impurity. The above obtained orange filtercake was slurried in EtOAc (80 mL) and stirred at 80 °C for 30 min. Then it was cooled to room t emperature and the precipitation was filtered. Yellow fine powder was obtained. |
Here is a chemical reaction formula: Reactants are amine:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N, amount is: 0.046300001442432404 MOLE;aryl halide:C1COCCN1CC2=CC=C(C=C2)Br, amount is: 0.053199999034404755 MOLE,Reagents are Base:CCC(C)(C)[O-].[Na+], amount is: 0.07410000264644623 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.004459999967366457 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.0018599999602884054 MOLE.Products are 0:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=CC=C(C=C4)CN5CCOCC5, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Tris(dibenzylideneacetone)dipalladium(0) (1.703 g, 1.86 mmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (2.58 g, 4.46 mmol) were dissolved in toluene (50 ml) in a 500 mL two-necked round-bottomed flask equipped with a condensor and activated at 50 °C for 40 min under argon. 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (12.84 g, 46.30 mmol), 4-(4-bromobenzyl)morpholine (13.64 g, 53.25 mmol), Sodium tert-pentoxide (8.16 g, 74.09 mmol) and extra toluene (250 mL) were added. The total volume of the reaction mixture was deoxygenized carefully by switching vacuum-argon 10-times and heated to 110 °C under argon. After 10 min the mixture turned into green. The reaction was monitored by HPLC, after 22 h only ca 65 %. The reactuion was stopped and the mixture was cooled to room temperature. Toluene was removed in vacuo. The residual was dissolved in dichloromethane ( 1.2 L) and extracted with water (2*1 L). The aqueous phase was extracted with EtOAc(600 mL). The combined orange organic phases were filtered through a celitepad and concetrated in vacuo. Dark orange brown sticky gum was obtained which solidified over 2 weeks. This solid was slurried in EtOAc (60 mL) at reflux point for 1 h, then it was cooled to rt slowly with vigorous stirring. Filtration afforded a light yellow solid and an orange filtrate. 0.5 g of the filtercake was purified by preparative HPLC, it afforded 303 mg light yellow solid which was submitted to PARD directly (EN01460-38-001). 1.8 g of the filtercake was purified by preparative HPLC, it afforded 1.02 g light yellow solid and 1.015 g was submitted to PARD directly in a standard bascoded bottle (EN01460-38-002) (barcode: 30152995). The residual material was used for recrystallization studies in the RSL group. |
Here is a chemical reaction formula: Reactants are amine:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N, amount is: 0.00018400000408291817 MOLE;aryl halide:C1COCCN1CC2=CC=C(C=C2)Br, amount is: 0.00019299999985378236 MOLE,Reagents are Base:CCC(C)(C)[O-].[Na+], amount is: 0.00029399999766610563 MOLE,Solvents are Solvent:CCCCOC(=O)C, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C, amount is: 9.200000022246968e-06 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 4.909999915980734e-06 MOLE.Products are 0:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=CC=C(C=C4)CN5CCOCC5, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Tris(dibenzylideneacetone)dipalladium(0) (4.5 mg, 4.91 µmol) and 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (4.38 mg, 9.20 µmol) were dissolved in butyl acetate (1.8 mL) in a 10 mL Schlenk tube and activated at 100 °C for 6 min under argon. Then 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (51 mg, 0.18 mmol), 4-(4-bromobenzyl)morpholine (49.5 mg, 0.19 mmol) and Sodium tert-pentoxide (32.4 mg, 0.29 mmol) were added. It was degassed again and stirred at 100 °C under argon. The reaction was followed by HPLC. After 4.5 h no conversion was observed. Hence the whole reaction mixture was discarded. |
Here is a chemical reaction formula: Reactants are amine:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N, amount is: 0.003599999938160181 MOLE;aryl halide:C1COCCN1CC2=CC=C(C=C2)Br, amount is: 0.0037799999117851257 MOLE,Reagents are Base:CCC(C)(C)[O-].[Na+], amount is: 6.479999865405262e-05 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 6.479999865405262e-05 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 5.400000009103678e-05 MOLE.Products are 0:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=CC=C(C=C4)CN5CCOCC5, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Tris(dibenzylideneacetone)dipalladium(0) (0.049 g, 54 µmol) and9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (0.037 g, 0.06 mmol) were dissolved in toluene (15 mL) in a 50 mL two-necked round-bottomed flask equipped with a condensor and activated at 100 °C for 6 min under argon. Then 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (0.998 g, 3.6 mmol), 4-(4-bromobenzyl)morpholine (0.968 g, 3.78 mmol), Sodium tert-pentoxide (0.634 g, 5.76 mmol) and toluene (20 mL) were added. The reaction mixture became sticky yellowish green maybe by addition of the base. It was degassed carefully and stirred at 100 °C under argon. In 1 hour the sticky mixture turned from yellowish green into orange brown muddy mixture. The reaction was followed by HPLC. After 22 h 98 % conversion was obtained. Then it was cooled to rt and filtered. The obtained dark brown crapy filtercake was discarded. The brown filtrate was diluted with dichloromethane (80 mL), extracted with water (3*100 mL), washed with brine (1*100 mL) and dried over Na2SO4. Filtration and concentration afforded orange solid (1.400 g). To this orange solid EtOAc (7 mL) was added and heat to 80 ºC. At 60 ºC it started to form light precipitation. Extra EtOAc (10 mL) was added and stirred at 80 ºC for 10 min. Then it was cooled to rt with a continuous stirring. The light precipitation was filtered off, washed with EtOAc (7 mL) and _n_ -pentane (15 mL), and dried in vacuo. Light yellow powder was obtained. |
Here is a chemical reaction formula: Reactants are amine:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N, amount is: 0.12999999523162842 MOLE;aryl halide:C1COCCN1CC2=CC=C(C=C2)Br, amount is: 0.13600000739097595 MOLE,Reagents are Base:CCC(C)(C)[O-].[Na+], amount is: 0.20800000429153442 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.0023399998899549246 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.0019499999471008778 MOLE.Products are 0:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=CC=C(C=C4)CN5CCOCC5, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Tris(dibenzylideneacetone)dipalladium(0) (1.786 g, 1.95 mmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (1.354 g, 2.34 mmol) were dissolved in toluene (40 mL) in a 100 mL two-necked round-bottomed flask equipped with a condensor and activated at 50 °C for 30 min under argon. In a 2 L reactor 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (36.0 g, 130 mmol), 4-(4-bromobenzyl)morpholine (34.8 g, 136 mmol), Sodium tert-pentoxide (22.91 g, 208.00 mmol) were dissolved in degassed toluene (960 mL) by heating at 100 °C. The preactivated catalyst solution was added to the mixture. It was put under nitrogen atmosphere carefully and stirred at 100 °C. The reaction was monitored by HPLC. After 20 h 38 % conversion was obtained. An extra batch of preactivated catalyst (3 %) in toluene (40 mL) was added and the mixture was stirred at 100 °C under nitrogen. After 52 h 92 % conversion was detected. Then the reaction mixture was cooled to room temperature, diluted with DCM (8 L) and extracted with water (3*5L). The separated organic phase was washed with brine and dried over Na2SO4. Filtration and concentration afforded orange solid which was slurried in EtOAc (100 mL) and stirred at reflux point for 30 min. Then it was cooled to room temperature and filtered. Yellow filtercake was obtained which was washed with EtOAc (150 ml). It was reslurried in EtOAc (100 mL) and stirred at reflux point for 30 min. Then it was cooled to room temperature and filtered. The filtercake was washed with EtOAc (150 ml) and dried in vacuo. Light yellow fine powder was obtained. |
Here is a chemical reaction formula: Reactants are aryl halide:C1COCCN1CC2=CC=C(C=C2)Br, amount is: 0.0010999999940395355 MOLE;amine:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N, amount is: 0.0010000000474974513 MOLE,Reagents are Base:CCC(C)(C)[O-].[Na+], amount is: 0.0014600000577047467 MOLE,Solvents are Solvent:COCCOC, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 0.009999999776482582 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 9.999999747378752e-06 MOLE.Products are 0:CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=CC=C(C=C4)CN5CCOCC5, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The aim of the reaction is only optimization and test. The reaction described below was carried out under argon atmosphere. Palladium(II) acetate (2.245 mg, 10.00 µmol) and (R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine (5.61 mg, 10.00 µmol) were mixed in DME (0.2 mL) in a 1.4 ml vial under argon and stirred for 1 minute at room temperature. The orange pre-mixed Pd-catalyst solution were added to a 10 mL Schlenk-tube containing 4-(4-bromobenzyl)morpholine (0.282 g, 1.1 mmol) and Sodium tert- pentoxide (0.161 g, 1.46 mmol) in DME (1.5 mL). Finally, 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (0.277 g, 1 mmol) was added and the bright orange reaction mixture was stirred at 90 °C. The mixture turned from bright orange into bright yellow in 1 h. The reaction was followed by HPLC. No reaction took place, hence the mixture was discarded. |
Here is a chemical reaction formula: Reactants are amine:CC1=C(C(=NN1C)C)N, amount is: 0.0006070000235922635 MOLE;aryl halide:CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C(F)(F)F)Cl, amount is: 0.00030300000798888505 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0003640000068116933 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 4.8499998229090124e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 2.429999949526973e-05 MOLE.Products are 0:CC1=C(C(=NN1C)C)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NC)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(2-chloro-5-(trifluoromethyl)pyridin-4-ylamino)-N-methylbenzamide (100 mg, 0.30 mmol), 1,3,5-trimethyl-1H-pyrazol-4-amine (76 mg, 0.61 mmol), cesium carbonate (119 mg, 0.36 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (28.1 mg, 0.05 mmol) and diacetoxypalladium (5.45 mg, 0.02 mmol) were suspended in dioxane (1.5 mL) and sealed into a tube. The reaction was degased, purged with nitrogen and heated to 100 °C for 18 hours. Reaction was filtered. The reaction mixture was purified by preparative HPLC using a Waters X-Bridge reverse-phase column (C-18, 5 microns silica, 19 mm diameter, 100 mm length, flow rate of 40 ml / minute) and decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. The fractions containing the desired compound were evaporated to dryness to afford N-methyl-2-(5-(trifluoromethyl)-2-(1,3,5-trimethyl-1H-pyrazol-4-ylamino)pyridin-4-ylamino)benzamide (31.0 mg, 24.43 %) as a pale yellow solid. |
Here is a chemical reaction formula: Reactants are aryl halide:CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl, amount is: 0.0013500000350177288 MOLE;amine:CC1=NN(C=C1N)C, amount is: 0.0016199999954551458 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0016199999954551458 MOLE,Solvents are Solvent:COCCOC, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 0.00014000000373926014 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 1.4000000192027073e-05 MOLE.Products are 0:CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NC)Cl)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1,3-dimethyl-1H-pyrazol-4-amine (180 mg, 1.62 mmol), 2-(2,5-dichloropyridin-4-ylamino)-N-methylbenzamide (400 mg, 1.35 mmol), Sodium t-Butoxide (156 mg, 1.62 mmol),(R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T- BUTYLPHOSPHINE (73.8 mg, 0.14 mmol) and diacetoxypalladium (24.26 mg, 0.11 mmol) were suspended in DME (8 mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 30 minutes in the microwave reactor and cooled to RT. Incomplete reaction, the reaction was heated to 150 °C for a further 1 hour in the microwave reactor and cooled to RT. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and fractions were evaporated to dryness. The crude product was then purified by Basic prep HPLC, fractions containing the desired compound were evaporated to dryness to afford 2-(5-chloro-2-(1,3-dimethyl-1H-pyrazol-4-ylamino)pyridin-4-ylamino)-N-methylbenzamide (267 mg, 53.3 %) as a brown solid. |
Here is a chemical reaction formula: Reactants are amine:COC1=C2C(=CC=C1)SC(=N2)N, amount is: 0.0012000000569969416 MOLE;aryl halide:C1=CC=C(C=C1)I, amount is: 0.0010000000474974513 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0020000000949949026 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 9.999999747378752e-05 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 2.9999999242136255e-05 MOLE.Products are 0:COC1=C2C(=CC=C1)SC(=N2)NC3=CC=CC=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-methoxybenzo[d]thiazol-2-amine (0.216 g, 1.20 mmol), iodobenzene (0.112 mL, 1.00 mmol), XANTPHOS (0.058 g, 0.10 mmol), Pd2(dba)3 (0.027 g, 0.03 mmol) and SODIUM TERT-BUTOXIDE (0.192 g, 2.00 mmol) placed in a sealed reaction via under an atmosphere of nitrogen and heated at 90ºC for 1 hour. LC/MS indicated mainly product, little SM. Cooled, diluted DCM and washed with water and brine. Org phase dried/MgSO4, filtered and evaporated. The crude product was purified by flash silica chromatography, eluting with dichloromethane. Pure fractions were evaporated to dryness to afford 4-methoxy-N- phenylbenzo[d]thiazol-2-amine (0.039 g, 15.22 %) as an colorless solid. EN01327-44-1 (0.039 g, 0.15 mmol, 15.22 %) Not sure why yield so low, crude lc/ms looked fine. Reaction left for several days before working up. |
Here is a chemical reaction formula: Reactants are amine:CC(C)(C)OC(=O)NC1CCNCC1, amount is: 0.0004990000161342323 MOLE;aryl halide:C1=CC2=NC=CC(=C2C=C1Cl)Cl, amount is: 0.0004490000137593597 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.001500000013038516 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 4.990000161342323e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 2.499999936844688e-05 MOLE.Products are 0:C1CN(CCC1N)C2=C3C=C(C=CC3=NC=C2)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: diacetoxypalladium (5.60 mg, 0.02 mmol) was added in one portion to tert-butyl piperidin-4-ylcarbamate (100 mg, 0.50 mmol), 4,6-dichloroquinoline (89 mg, 0.45 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (28.9 mg, 0.05 mmol) and cesium carbonate (488 mg, 1.50 mmol) in DMA (5 mL). The resulting mixture was stirred at 150 °C for 1 hour. LCMS analysis showed formation of a small amount of the desired product. The mixture was heated for a further 2 hours, after which time LCMS analysis showed loss of this small peak. Abandoned. |
Here is a chemical reaction formula: Reactants are amine:CC(C)(C)OC(=O)N1CC(C1)OC2=CC(=C(C=C2)N)OC, amount is: 0.0003769999893847853 MOLE;aryl halide:C1=CC2=NC=C(N2C=C1)C3=NC(=NC=C3Cl)Cl, amount is: 0.0003769999893847853 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 3.020000076503493e-05 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 3.020000076503493e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 1.5100000382517464e-05 MOLE.Products are 0:COC1=C(C=CC(=C1)OC2CNC2)NC3=NC=C(C(=N3)C4=CN=C5N4C=CC=C5)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3-(2,5-dichloropyrimidin-4-yl)imidazo[1,2-a]pyridine (100 mg, 0.38 mmol) _,_ tert-butyl 3-(4-amino-3-methoxyphenoxy)azetidine-1-carboxylate (111 mg, 0.38 mmol) _,_ CESIUM CARBONATE (246 mg, 0.75 mmol) _,_ diacetoxypalladium (3.39 mg, 0.02 mmol) _and_ 9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE (17.46 mg, 0.03 mmol) ___were_ ___suspended_ _in_ 1,4-dioxane (1 ml) _and degased with argon.The reaction was heated from 60°C to 105°C for 3 hours.Doubt about the LCMS,deprotection of the BOC with TFA to confirm the dialkylation._ No good product |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CN=C(C=C1Cl)Cl, amount is: 0.06759999692440033 MOLE;amine:C1=CC=C(C=C1)N, amount is: 0.06759999692440033 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.13500000536441803 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.00203000009059906 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.0013500000350177288 MOLE.Products are 0:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: diacetoxypalladium (0.303 g, 1.35 mmol) was added in one portion to a degassed mixture of 2,4-dichloropyridine (10 g, 67.57 mmol), aniline (6.29 g, 67.57 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (1.173 g, 2.03 mmol) and cesium carbonate (44.0 g, 135.14 mmol) in dioxane (250 mL) under argon. The resulting mixture was stirred at 100 °C for 24 hours. The mixture was then cooled to room temperature, filtered and concentrated to dryness to give the crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 5% MeOH in DCM. Pure fractions were evaporated to dryness to afford 4-chloro-N-phenylpyridin-2-amine (7.72 g, 55.8 %) as a pale orange solid. |
Here is a chemical reaction formula: Reactants are amine:CN1C(=CC=N1)N, amount is: 0.0006070000235922635 MOLE;aryl halide:CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C(F)(F)F)Cl, amount is: 0.00030300000798888505 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0003640000068116933 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 4.8499998229090124e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 2.429999949526973e-05 MOLE.Products are 0:CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C(F)(F)F)NC3=CC=NN3C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(2-chloro-5-(trifluoromethyl)pyridin-4-ylamino)-N-methylbenzamide (100 mg, 0.30 mmol), 1-methyl-1H-pyrazol-5-amine (58.9 mg, 0.61 mmol), cesium carbonate (119 mg, 0.36 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (28.1 mg, 0.05 mmol) and diacetoxypalladium (5.45 mg, 0.02 mmol) were suspended in dioxane (1.5 mL) and sealed into a tube. The reaction was degased, purged with nitrogen and heated to 100 °C for 18 hours. Reaction was filtered. The reaction mixture was purified by preparative HPLC using a Waters X-Bridge reverse-phase column (C-18, 5 microns silica, 19 mm diameter, 100 mm length, flow rate of 40 ml / minute) and decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. The fractions containing the desired compound were evaporated to dryness to afford N-methyl-2-(2-(1-methyl-1H-pyrazol-5-ylamino)-5-(trifluoromethyl)pyridin-4-ylamino)benzamide (62.0 mg, 52.4 %) [salt] as a pale orange solid. |
Here is a chemical reaction formula: Reactants are amine:CNC(=O)C1=CC=CC=C1N, amount is: 0.014000000432133675 MOLE;aryl halide:C1=C(C(=CN=C1Cl)C(F)(F)F)I, amount is: 0.014000000432133675 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.01679999940097332 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.002240000059828162 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.001120000029914081 MOLE.Products are 0:CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C(F)(F)F)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-chloro-4-iodo-5-(trifluoromethyl)pyridine (4.305 g, 14.00 mmol), 2-amino-N- methylbenzamide (2.103 g, 14.00 mmol), diacetoxypalladium (0.251 g, 1.12 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (1.296 g, 2.24 mmol) and cesium carbonate (5.47 g, 16.80 mmol) were mixed together in dioxane (80 mL). Reaction was degassed with argon and was stirred at 90 °C overnight (15 hours) under argon. Reaction was filtered, washed with CH2Cl2 and filtrate was concentrated to dryness. The crude product was purified by flash chromatography on silica gel eluting with 10 to 40% ethyl acetate in petroleum ether. The solvent was evaporated to dryness to afford 2-(2-chloro-5-(trifluoromethyl)pyridin-4-ylamino)-N-methylbenzamide (3.39 g, 73.4 %) as a white crystalline solid. |
Here is a chemical reaction formula: Reactants are amine:CNC(=O)C1=CC=CC=C1N, amount is: 0.02280000038444996 MOLE;aryl halide:C1=C(C(=CN=C1Cl)C(F)(F)F)I, amount is: 0.02280000038444996 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.027300000190734863 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.003640000009909272 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.001820000004954636 MOLE.Products are 0:CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C(F)(F)F)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-chloro-4-iodo-5-(trifluoromethyl)pyridine (7 g, 22.77 mmol), 2-amino-N- methylbenzamide (3.42 g, 22.77 mmol), diacetoxypalladium (0.409 g, 1.82 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (2.108 g, 3.64 mmol) and cesium carbonate (8.90 g, 27.32 mmol) were mixed together in dioxane (140 mL). Reaction was degassed with nitrogen and was stirred at 90 °C overnight under nitrogen. Reaction was filtered, washed with CH2Cl2 and filtrate was concentrated to dryness. The crude product was purified by flash chromatography on silica gel eluting with 10 to 50% ethyl acetate in petroleum ether. The solvent was evaporated to dryness to afford 2-(2-chloro-5-(trifluoromethyl)pyridin-4-ylamino)-N-methylbenzamide (5.06 g, 67.4 %) as a pale yellow solid. |
Here is a chemical reaction formula: Reactants are amine:CNC(=O)C1=CC=CC=C1N, amount is: 0.0016299999551847577 MOLE;aryl halide:C1=C(C(=CN=C1Cl)C(F)(F)F)I, amount is: 0.0016299999551847577 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0019499999471008778 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.00026000000070780516 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.00013000000035390258 MOLE.Products are 0:CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C(F)(F)F)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-chloro-4-iodo-5-(trifluoromethyl)pyridine (500 mg, 1.63 mmol), 2-amino-N- methylbenzamide (244 mg, 1.63 mmol), diacetoxypalladium (29.2 mg, 0.13 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (151 mg, 0.26 mmol) and cesium carbonate (636 mg, 1.95 mmol) were mixed together in dioxane (10 mL). Reaction was degassed with nitrogen and was stirred at 90 °C overnight under nitrogen. Reaction was filtered, washed with CH2Cl2 and filtrate was concentrated to dryness. The crude product was purified by flash chromatography on silica gel eluting with 10 to 50% ethyl acetate in petroleum ether. The solvent was evaporated to dryness to afford 2-(2-chloro-5-(trifluoromethyl)pyridin-4-ylamino)-N-methylbenzamide (340 mg, 63.4 %) as a pale yellow solid. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CN=C(C=C1C(F)(F)F)Br, amount is: 0.0011899999808520079 MOLE;amine:CC(C)(C)OC(=O)N1CCC(CC1)(CN=C(C2=CC=CC=C2)C3=CC=CC=C3)C(=O)N, amount is: 0.0011899999808520079 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0016599999507889152 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 5.339999916031957e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 3.559999822755344e-05 MOLE.Products are 0:CC(C)(C)OC(=O)N1CCC(CC1)(CN=C(C2=CC=CC=C2)C3=CC=CC=C3)C(=O)NC4=NC=CC(=C4)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: tert-butyl 4-carbamoyl-4-((diphenylmethyleneamino)methyl)piperidine-1-carboxylate (500 mg, 1.19 mmol), 2-bromo-4-(trifluoromethyl)pyridine (268 mg, 1.19 mmol), and cesium carbonate (541 mg, 1.66 mmol) were suspended in dioxane (2 mL) . The reaction was purged with nitrogen for 10 minutes then 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (30.9 mg, 0.05 mmol) and palladium(II) acetate (7.99 mg, 0.04 mmol) were added. The reaction was heated at 90 °C for 48 hours. The reaction was cooled to room temperature, diluted with DCM, filtered and concentrated. The crude product was purified by flash silica chromatography, elution gradient 0 to 40% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford tert-butyl 4-((diphenylmethyleneamino)methyl)-4-(4-(trifluoromethyl)pyridin-2-ylcarbamoyl)piperidine-1-carboxylate (480 mg, 71.4 %) as a white solid. |
Here is a chemical reaction formula: Reactants are amine:CC(=O)N1CCNCC1, amount is: 0.003010000102221966 MOLE;aryl halide:CC1=C(C=CC=C1Br)[N+](=O)[O-], amount is: 0.002309999894350767 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.003470000112429261 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.00034699999378062785 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.00023099999816622585 MOLE.Products are 0:CC1=C(C=CC=C1[N+](=O)[O-])N2CCN(CC2)C(=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1-bromo-2-methyl-3-nitrobenzene (500 mg, 2.31 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (201 mg, 0.35 mmol) and cesium carbonate (1131 mg, 3.47 mmol) and diacetoxypalladium (52.0 mg, 0.23 mmol) were dissolved in toluene (10 mL) and sealed into a microwave tube degazed and purged with argon. The reaction was heated to 100 °C, over a period of 12 hours. The reaction mixture was cooled down to room temperature, filtered and the residue was evaporated. The crude product was purified by flash chromatography on silica gel eluting with 0 to 10% methanol in dichloromethane. The solvent was evaporated to dryness to afford 1-(4-(2-methyl-3-nitrophenyl)piperazin-1-yl)ethanone (600 mg, 98 %) as a solid. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=C(C(=CN=C1Cl)Cl)I, amount is: 0.003650000086054206 MOLE;amine:CNC(=O)C1=C(C=CC(=C1)F)N, amount is: 0.0034799999557435513 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.006949999835342169 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.00020900000527035445 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.00013899999612476677 MOLE.Products are 0:CNC(=O)C1=C(C=CC(=C1)F)NC2=CC(=NC=C2Cl)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: palladium acetate (31.2 mg, 0.14 mmol) was added to 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (121 mg, 0.21 mmol), Cesium carbonate (2266 mg, 6.95 mmol), 2-amino-5-fluoro-N-methylbenzamide (585 mg, 3.48 mmol) and 2,5-dichloro-4-iodopyridine (1000 mg, 3.65 mmol) in dioxane (20 mL) under nitrogen. The resulting suspension was stirred at 80 °C for 18hrs then cooled. Product appeared to be out of solution. Product and bis product suggested. Disappointing! The reaction mixture was evaporated to dryness and redissolved in EtOAc (100 mL), and washed sequentially with saturated Na2CO3 (50 mL), water (50 mL), and saturated brine (50 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 50% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford desired product as an beige solid. |
Here is a chemical reaction formula: Reactants are aryl halide:C1CCC(CC1)NC(=O)C2=CN=C(C=C2)Cl, amount is: 0.0012600000482052565 MOLE;amine:C1=CC(=CC=C1C#N)N, amount is: 0.001509999972768128 MOLE,Reagents are Base:CC(C)(C)[O-].[K+], amount is: 0.0025100000202655792 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.00025099999038502574 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.00012599999899975955 MOLE.Products are 0:C1CCC(CC1)NC(=O)C2=CN=C(C=C2)NC3=CC=C(C=C3)C#N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In a 50 mL round-bottomed flask a TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.115 g, 0.13 mmol),POTASSIUM TERT-BUTOXIDE (0.282 g, 2.51 mmol)and BINAP (0.157 g, 0.25 mmol) in dry 1,4-dioxane (10 mL) was mixed under N2.Followed by 6-chloro-N-cyclohexylnicotinamide (.300 g, 1.26 mmol) and 4-aminobenzonitrile (0.178 g, 1.51 mmol) was added and resulting mixture(dark brown) was heated at 100oC for 3 hrs.LCMS analysis showed the formation of required product.Reaction stopped,crude was passed through celite and washed with dioxane and finally with methanol.The filtrate was dried and dissolved in 3 ml DMSO for Waters MS Purification system.Pure fractions collected and concentrated.A White solid obtained as a product 6-(4-cyanophenylamino)-N-cyclohexylnicotinamide (0.040 g, 9.93 %).32 mg of above product was submitted for MGyrx2 projetct.LCMS/NMR confirmed the product. |
Here is a chemical reaction formula: Reactants are aryl halide:CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C(F)(F)F)Cl, amount is: 0.00028899998869746923 MOLE;amine:CC1=NN(C=C1N)C, amount is: 0.00034699999378062785 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.00040499999886378646 MOLE,Solvents are Solvent:COCCOC, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 2.9999999242136255e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 2.9999999242136255e-05 MOLE.Products are 0:CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)C(F)(F)F)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Palladium(II) acetate (7.79 mg, 0.03 mmol), (R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine (19.46 mg, 0.03 mmol), Cesium carbonate (0.032 mL, 0.40 mmol), 1,3-dimethyl-1H-pyrazol-4-amine (38.6 mg, 0.35 mmol) and 2-(2-chloro-5-(trifluoromethyl)pyridin-4-ylamino)-N-methoxybenzamide (100 mg, 0.29 mmol) were suspended in DME (2.5 mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 30 minutes in the microwave reactor and cooled to RT. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and pure fractions were evaporated to dryness to afford crude product as a orange gum. The sample was given to the purification group to be purified by preparative HPLC. Fractions containing the desired compound were evaporated to dryness to afford 2-(2-(1,3-dimethyl-1H-pyrazol-4-ylamino)-5-(trifluoromethyl)pyridin-4-ylamino)-N-methoxybenzamide (13.60 mg, 11.18 %) as a tan gum. The sample was not pure enough to register so will be re-made. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CN=C(N=C1Cl)Cl, amount is: 0.001339999958872795 MOLE;amine:C1CC2=CC=CC=C2NC1, amount is: 0.001339999958872795 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0020099999383091927 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.0001340000017080456 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 6.710000161547214e-05 MOLE.Products are 0:C1CC2=CC=CC=C2N(C1)C3=NC(=NC=C3)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2,4-dichloropyrimidine (200 mg, 1.34 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (78 mg, 0.13 mmol), Tris(dibenzylideneacetone)dipalladium(0) (61.5 mg, 0.07 mmol) and Cesium carbonate (656 mg, 2.01 mmol) was added to a microwave vial. toluene (2 mL) was added. 1,2,3,4-tetrahydroquinoline (179 mg, 1.34 mmol) was added. Heated to 120ºC in microwave oven for 90min. Crude filtered through celite and then added to prepHPLC. 30-70% acetonitrile in water. Pure fractions pooled and then freezedried over night. Yielded 1-(2-chloropyrimidin-4-yl)-1,2,3,4-tetrahydroquinoline (24.00 mg, 7.28 %) |
Here is a chemical reaction formula: Reactants are amine:CC1=NN(C=C1N)C, amount is: 0.0003640000068116933 MOLE;aryl halide:CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C(F)(F)F)Cl, amount is: 0.00030300000798888505 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0004250000056345016 MOLE,Solvents are Solvent:COCCOC, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 3.9999998989515007e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 3.9999998989515007e-05 MOLE.Products are 0:CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NC)C(F)(F)F)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Palladium(II) acetate (8.17 mg, 0.04 mmol), (R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine (20.40 mg, 0.04 mmol), Sodium tert-butoxide (0.052 mL, 0.42 mmol), 1,3-dimethyl-1H-pyrazol-4-amine (40.5 mg, 0.36 mmol) and 2-(2-chloro-5-(trifluoromethyl)pyridin-4-ylamino)-N-methylbenzamide (100 mg, 0.30 mmol) were suspended in DME (2.5 mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 30 minutes in the microwave reactor and cooled to RT. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and pure fractions were evaporated to dryness to afford 2-(2-(1,3-dimethyl-1H-pyrazol-4-ylamino)-5-(trifluoromethyl)pyridin-4-ylamino)-N-methylbenzamide (41.3 mg, 33.7 %) as a orange gum. The sample was given to the purification group to be purified by preparative HPLC. Fractions containing the desired compound were evaporated to dryness to afford 2-(2-(1,3-dimethyl-1H-pyrazol-4-ylamino)-5-(trifluoromethyl)pyridin-4-ylamino)-N-methylbenzamide (41.3 mg, 33.7 %) as a yellow solid. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC(=CC=C1C#N)C2=CSC(=N2)Br, amount is: 0.0003769999893847853 MOLE;amine:C1COC(=O)N1, amount is: 0.0005660000024363399 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.001129999989643693 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 3.769999966607429e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 2.6399999114801176e-05 MOLE.Products are 0:C1COC(=O)N1C2=NC(=CS2)C3=CC=C(C=C3)C#N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-(2-bromothiazol-4-yl)benzonitrile (100 mg, 0.38 mmol), 2-Oxazolidinone (49.3 mg, 0.57 mmol), diacetoxypalladium (5.93 mg, 0.03 mmol), cesium carbonate (369 mg, 1.13 mmol), water (10 µl) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (21.82 mg, 0.04 mmol) were suspended in dioxane (2 mL), thoroughly degassed and sealed into a microwave tube and stirred at RT for 20 mins. The reaction was then heated to 150 °C for 10 minutes in the microwave reactor and cooled to RT. Load of rubbish... ABANDONED |
Here is a chemical reaction formula: Reactants are amine:CNC(=O)C1=C(C=C(C=C1)F)NC2=CC(=NC=C2Cl)Cl, amount is: 0.0005249999812804163 MOLE;aryl halide:CC1=NN(C=C1N)C.Cl.Cl, amount is: 0.0010499999625608325 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0011599999852478504 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 8.399999933317304e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 4.199999966658652e-05 MOLE.Products are 0:CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C=CC(=C3)F)C(=O)NC)Cl)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(2,5-dichloropyridin-4-ylamino)-4-fluoro-N-methylbenzamide (165 mg, 0.53 mmol), 1,3-dimethyl-1H-pyrazol-4-amine dihydrochloride (193 mg, 1.05 mmol), cesium carbonate (376 mg, 1.16 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (48.6 mg, 0.08 mmol) and diacetoxypalladium (9.43 mg, 0.04 mmol) were suspended in dioxane (3 mL) and sealed into a tube. The reaction was degased, purged with nitrogen and heated to 100 °C for 16 hours => _reaction not complete._ (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine), diacetoxypalladium and cesium carbonate were added. The reaction was degased, purged with nitrogen and heated to 110 °C for 4 hours => _reaction still not complete, no progress ..._ Reaction was filtered, washed with CH2Cl2 and concentrated to dryness. The reaction mixture was purified by preparative HPLC using a Waters X-Bridge reverse-phase column (5 microns silica, 30 mm diameter, 150 mm length) and decreasingly polar mixtures of water (containing 1% acetic acid) and acetonitrile as eluent. The pure fractions were combined, basified with a saturated aqueous solution of NaHCO3 and extracted with CH2Cl2. Organic layer was washed with brine, dried over MgSO4 and concentrated to dryness to afford 2-(5-chloro-2-(1,3-dimethyl-1H-pyrazol-4-ylamino)pyridin-4-ylamino)-4-fluoro- N-methylbenzamide (8.00 mg, 3.92 %) as a green dry film. |
Here is a chemical reaction formula: Reactants are aryl halide:C1CC1C(=O)NC2=NC=CC(=C2)Cl, amount is: 0.00072900002123788 MOLE;amine:C1OC2=CC=CC(=C2O1)N, amount is: 0.00072900002123788 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0014600000577047467 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 8.749999688006938e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 3.650000144261867e-05 MOLE.Products are 0:C1CC1C(=O)NC2=NC=CC(=C2)NC3=C4C(=CC=C3)OCO4, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: benzo[d][1,3]dioxol-4-amine (100 mg, 0.73 mmol), N-(4-chloropyridin-2-yl)cyclopropanecarboxamide (143 mg, 0.73 mmol), XANTPHOS (50.6 mg, 0.09 mmol), PALLADIUM(II) ACETATE (8.19 mg, 0.04 mmol) and CESIUM CARBONATE (475 mg, 1.46 mmol) were suspended in DMA (3mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 1.5 hours in the microwave reactor and cooled to RT. LC/MS showed completion. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 0.35M NH3/MeOH and pure fractions were evaporated to dryness to afford N-(4-(benzo[d][1,3]dioxol-4-ylamino)pyridin-2-yl)cyclopropanecarboxamide as a brown oil. The crude product was purified by preparative HPLC using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford N-(4-(benzo[d][1,3]dioxol-4-ylamino)pyridin-2-yl)cyclopropanecarboxamide (110 mg, 50.7 %) as a cream solid. |
Here is a chemical reaction formula: Reactants are aryl halide:COC(=O)C1=CC=C(C=C1)OCC2=C(C=CC=N2)Br, amount is: 0.001120000029914081 MOLE;amine:CN1CCNCC1, amount is: 0.0016799999866634607 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0022299999836832285 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.000446999998530373 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.0002229999954579398 MOLE.Products are 0:CN1CCN(CC1)C2=C(N=CC=C2)COC3=CC=C(C=C3)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of methyl 4-((3-bromopyridin-2-yl)methoxy)benzoate (360 mg, 1.12 mmol), Pd2dba3 (205 mg, 0.22 mmol), BINAP (278 mg, 0.45 mmol), cesium carbonate (728 mg, 2.23 mmol) and 1-methylpiperazine (168 mg, 1.68 mmol) in DMA (10 mL) was stirred at 100 °C for overnight. Sat. NaHCO3 aq was added to the mixture, extracted with ethyl acetate three times, the combined organics were dried over anhydrous Na2SO4, filtered, the filtrate was conc. in vacuo, the residue was purified with ISCO (50% ethyl acetate in hexant to 100% ethyl acetate to 40% mthanol in ethyl acetate) to yield a brown oil as methyl 4-((3-(4-methylpiperazin-1-yl)pyridin-2-yl)methoxy)benzoate (245 mg, 64.2 %). |
Here is a chemical reaction formula: Reactants are amine:CN(C)[C@H]1CCNC1, amount is: 0.0027699999045580626 MOLE;aryl halide:C1=CC(=C(C=C1Cl)Br)C#N, amount is: 0.002309999894350767 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.004619999788701534 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.0004619999963324517 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.00023099999816622585 MOLE.Products are 0:CN(C)[C@H]1CCN(C1)C2=C(C=CC(=C2)Cl)C#N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-bromo-4-chlorobenzonitrile (500 mg, 2.31 mmol), (S)-N,N-dimethylpyrrolidin-3-amine (317 mg, 2.77 mmol), cesium carbonate (1505 mg, 4.62 mmol), tris(dibenzylideneacetone)dipalladium(0) (212 mg, 0.23 mmol) and BINAP (288 mg, 0.46 mmol) in toluene (15 mL) was stirred at 100 °C for overnight. Conc. in vacuo, the residue was purified with ISCO (100% ethyl acetate to 30% methanol in ethyl acetate) to yield a light yellow solid as (S)-4-chloro-2-(3-(dimethylamino)pyrrolidin-1-yl)benzonitrile (400 mg, 69.3 %). |
Here is a chemical reaction formula: Reactants are amine:CN1CCC2=C(C1=O)C(=CC=C2)N, amount is: 0.00020199999562464654 MOLE;aryl halide:CC1=NN(C=C1NC2=NC=C(C(=C2)Cl)C#N)C, amount is: 0.00010099999781232327 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 1.0099999599333387e-05 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 1.0099999599333387e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 5.0499997996666934e-06 MOLE.Products are 0:CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC4=C3C(=O)N(CC4)C)C#N)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 8-amino-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (35.6 mg, 0.20 mmol), 4-chloro-6-(1,3-dimethyl-1H-pyrazol-4-ylamino)nicotinonitrile (25 mg, 0.10 mmol), diacetoxypalladium (1.133 mg, 5.05 µmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (5.84 mg, 10.09 µmol) and cesium carbonate (39.5 mg, 0.12 mmol) were dissolved in dioxane (0.5 mL) and sealed into a microwave tube. nitrogen was let to bubble into the mixture then the reaction was heated to 100 °C for 90 minutes. Crude LCMS showed the expected product P3 and no hydrolysis by-product at all like in _EN01775-20_ !! The reaction mixture was purified by preparative HPLC using a Waters X-Bridge reverse-phase column (C-18, 5 microns silica, 19 mm diameter, 100 mm length, flow rate of 40 ml / minute) and decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. **10 days later** , the fractions containing the desired compound were evaporated to dryness to afford impure 6-(1,3-dimethyl-1H-pyrazol-4-ylamino)-4-(2-methyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-8-ylamino)nicotinonitrile (13.00 mg, 33.2 %): it has probably gone off after 10 days in solution (aqueous ammonium carbonate and acetonitrile) ENCOURAGING, THOUGH. |
Here is a chemical reaction formula: Reactants are amine:COC1=C(C=CC(=C1)N2CCOCC2)N, amount is: 0.0007600000244565308 MOLE;aryl halide:CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl, amount is: 0.000506000011228025 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0010100000072270632 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 5.059999966761097e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 2.5299999833805487e-05 MOLE.Products are 0:CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)NC3=C(C=C(C=C3)N4CCOCC4)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-methoxy-4-morpholinoaniline (158 mg, 0.76 mmol), 2-(2,5-dichloropyridin-4-ylamino)-N-methylbenzamide (150 mg, 0.51 mmol),diacetoxypalladium (5.69 mg, 0.03 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (29.3 mg, 0.05 mmol) and cesium carbonate (330 mg, 1.01 mmol) were weighed out in a microwave vial and sealed. dioxane (3 mL) was added and argon was let to bubble for 5 minutes at rt. The resulting mixture was stirred at 110 °C for 1 hour. The reaction mixture was allowed to cool to room temperature and concentrated in presence of decalite speed plus. The crude product was purified by flash chromatography on silica gel eluting with 0 to 4% methanol in ethyl acetate/DCM (1/1). The solvent was evaporated to dryness. The foam was triturated in terbutyl methyl ether and the resulting precipitate was collected by filtration and washed with tBuOMe to afford 2-(5-chloro-2-(2-methoxy-4-morpholinophenylamino)pyridin-4-ylamino)-N-methylbenzamide (193 mg, 81 %) as a pale pink solid. |
Here is a chemical reaction formula: Reactants are aryl halide:CC1=C(C=CC(=C1)F)Br, amount is: 0.010599999688565731 MOLE;amine:CC(C)(C)OC(=O)N1CCNCC1, amount is: 0.01269999984651804 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.01590000092983246 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.0012700000079348683 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.0006350000039674342 MOLE.Products are 0:CC1=C(C=CC(=C1)F)N2CCN(CC2)C(=O)OC(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In a 200ml flask was added 1-bromo-4-fluoro-2-methylbenzene (2 g, 10.58 mmol) and TERT-BUTYL 1-PIPERAZINECARBOXYLATE (2.365 g, 12.70 mmol), CESIUM CARBONATE (5.17 g, 15.87 mmol) , BINAP (0.791 g, 1.27 mmol) 18-CROWN-6 (0.336 g, 1.27 mmol), followed by toluene (25 ml). Degass the mixture. TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.581 g, 0.63 mmol) was added. Heat at 110oC under nitrogen in an oil bath for overnight. The reaction mixture was diluted with ethyl acetate and filtered through celite. The Celite was washed with EtOAC. The EtOAC was concentrated down to give a brown oil. The crude product was purified by silica gel column(40g) and was eluted with 0% EtOAC/Hexane -50% EtOAC/Hexane. Yield: 0.5g Yellow oil. |
Here is a chemical reaction formula: Reactants are amine:CC(C)(C)OC(=O)N1CCNCC1, amount is: 0.004360000137239695 MOLE;aryl halide:C1=CC(=C(C=C1F)C(F)(F)F)Br, amount is: 0.0036299999337643385 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.005450000055134296 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.0004360000020824373 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.00021800000104121864 MOLE.Products are 0:CC(C)(C)OC(=O)N1CCN(CC1)C2=C(C=C(C=C2)F)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In a 100ml sealtube was added 1-bromo-4-fluoro-2-(trifluoromethyl)benzene (0.91 g, 3.63 mmol), CESIUM CARBONATE (1.775 g, 5.45 mmol), CESIUM CARBONATE (1.775 g, 5.45 mmol), BINAP (0.271 g, 0.44 mmol), TERT-BUTYL 1-PIPERAZINECARBOXYLATE (0.812 g, 4.36 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.200 g, 0.22 mmol) and 18-CROWN-6 (0.115 g, 0.44 mmol). Followed by 15mL toluene. The mixture was degassed by N2 bubbling for 15min. The reaction mixture was heated at 110oC under nitrogen in an oil bath for overnight. The reaction mixture was diluted with ethyl acetate and filtered through celite. The Celite was washed with EtOAC. The EtOAC was concentrated down to give a brown oil. The crude product was purified by silica gel column(40g) and was eluted with 0% EtOAC/Hexane -25% EtOAC/Hexane. Yield: 0.93g Yellow oil. . |
Here is a chemical reaction formula: Reactants are amine:CC(=O)N1CC2CNCC(C1)O2, amount is: 0.00021300000662449747 MOLE;aryl halide:COC1=C(C=C(C=C1)Br)[N+](=O)[O-], amount is: 0.0001939999929163605 MOLE,Reagents are Base:[O-]P(=O)([O-])[O-].[K+].[K+].[K+], amount is: 0.000291000003926456 MOLE,Solvents are Solvent:COCCOC, amount is: 0.0 ,Catalysts are metal and ligand:C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4, amount is: 3.099999958067201e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 1.9400000383029692e-05 MOLE.Products are 0:CC(=O)N1CC2CN(CC(C1)O2)C3=CC(=C(C=C3)OC)[N+](=O)[O-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1-(9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl)ethanone (36.3 mg, 0.21 mmol), 4-bromo-1-methoxy-2-nitrobenzene (45 mg, 0.19 mmol), diacetoxypalladium (4.35 mg, 0.02 mmol), biphenyl-2-yldicyclohexylphosphine (10.88 mg, 0.03 mmol) and potassium phosphate (61.8 mg, 0.29 mmol) in DME (0.5 mL) were degassed with nitrogen and stirred at 80 °C overnight => _no product formed, degradation_ **_ABANDONED_** |
Here is a chemical reaction formula: Reactants are aryl halide:CC1=C(C(=NC(=N1)N)Cl)CC2=CC=C(C=C2)CC#N, amount is: 0.0007329999934881926 MOLE;amine:CCC[C@@H](CO)N, amount is: 0.0014700000174343586 MOLE,Reagents are Base:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0014700000174343586 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 7.329999789362773e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 3.6699999327538535e-05 MOLE.Products are 0:CCC[C@@H](CO)NC1=NC(=NC(=C1CC2=CC=C(C=C2)CC#N)C)N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Palladium(II) acetate (8.23 mg, 0.04 mmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (42.4 mg, 0.07 mmol) were added to dioxane (3 mL) and the solution was stirred at room temperature for 10 minutes. 2-(4-((2-amino-4-chloro-6-methylpyrimidin-5-yl)methyl)phenyl)acetonitrile (200 mg, 0.73 mmol), (S)-(+)-2-Amino-1-pentanol (151 mg, 1.47 mmol) and POTASSIUM CARBONATE (203 mg, 1.47 mmol) were added and the mixture was heated at 100 °C for 15 hours. LCMS showed no product and reaction not progressed. |
Here is a chemical reaction formula: Reactants are aryl halide:CC1=C(C(=NC(=N1)/N=C/N(C)C)Cl)CC2=CC=C(C=C2)CC#N, amount is: 0.0007319999858736992 MOLE;amine:CC[C@H]1CNC(=O)O1, amount is: 0.0014600000577047467 MOLE,Reagents are Base:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0014600000577047467 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 7.31999971321784e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 3.65999985660892e-05 MOLE.Products are 0:CC[C@H]1CN(C(=O)O1)C2=NC(=NC(=C2CC3=CC=C(C=C3)CC#N)C)/N=C/N(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Palladium(II) acetate (8.22 mg, 0.04 mmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (42.4 mg, 0.07 mmol) were added to dioxane (3 mL) and the solution was stirred at room temperature for 10 minutes.(E)-N'-(4-chloro-5-(4-(cyanomethyl)benzyl)-6-methylpyrimidin-2-yl)-N,N-dimethylformimidamide (240 mg, 0.73 mmol), (S)-5-ethyloxazolidin-2-one (169 mg, 1.46 mmol) and POTASSIUM CARBONATE (202 mg, 1.46 mmol) were added and the mixture was heated at 100 °C for 1 hour. The solvent was evaporated under reduced pressure and the crude product was purified by flash silica chromatography, elution gradient 2 to 5% methanol in dichloromethane. Pure fractions were evaporated to dryness to afford (S,E)-N'-(5-(4-(cyanomethyl)benzyl)-4-(5-ethyl-2-oxooxazolidin-3-yl)-6-methylpyrimidin-2-yl)-N,N-dimethylformimidamide (136 mg, 45.7 %) as a colorless solid. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=C(C(=CN=C1Cl)Cl)I, amount is: 0.000547999981790781 MOLE;amine:CNC(=O)C1=C(C=C(C=C1)F)N, amount is: 0.000547999981790781 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0008219999726861715 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 5.4799998906673864e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 2.7399999453336932e-05 MOLE.Products are 0:CNC(=O)C1=C(C=C(C=C1)F)NC2=CC(=NC=C2Cl)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: diacetoxypalladium (6.15 mg, 0.03 mmol) was added to a stirred suspension of 2,5-dichloro-4-iodopyridine (150 mg, 0.55 mmol), 2-amino-4-fluoro-N- methylbenzamide (92 mg, 0.55 mmol) (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (31.7 mg, 0.05 mmol) and cesium carbonate (268 mg, 0.82 mmol) in 1,4-dioxane (2.5 mL) under nitrogen. The resulting suspension was stirred at 100 °C for 16 hours. The mixture was cooled to RT; filtered the solvent was evaporated. The crude product was absorbed on silica gel and purified by flash chromatography on silica gel eluting with 20 to 80% ethyl acetate in petroleum ether. The solvent was evaporated to dryness to afford 2-(2,5-dichloropyridin-4-ylamino)-4-fluoro-N-methylbenzamide (60.0 mg, 34.9 %) as a beige solid. |
Here is a chemical reaction formula: Reactants are amine:CNC(=O)C1=C(C=C(C=C1)F)N, amount is: 0.0010000000474974513 MOLE;aryl halide:C1=C(C(=CN=C1Cl)Cl)I, amount is: 0.0009130000253207982 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0013699999544769526 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 9.129999671131372e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 4.5600001612911e-05 MOLE.Products are 0:CNC(=O)C1=C(C=C(C=C1)F)NC2=CC(=NC=C2Cl)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2,5-dichloro-4-iodopyridine (250 mg, 0.91 mmol), 2-amino-4-fluoro-N- methylbenzamide (169 mg, 1.00 mmol) diacetoxypalladium (10.25 mg, 0.05 mmol) (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (52.8 mg, 0.09 mmol) and cesium carbonate (446 mg, 1.37 mmol) were dissolved in 1,4-dioxane (2.5 mL) and sealed into a microwave tube. The reaction was degased, purged with nitrogen and heated to 140 °C over a period of 30 minutes in the microwave reactor. The mixture was cooled to RT; filtered the solvent was evaporated. The crude product was absorbed on silica gel and purified by flash chromatography on silica gel eluting with 20 to 80% ethyl acetate in petroleum ether. The solvent was evaporated to dryness to afford 2-(2,5-dichloropyridin-4-ylamino)-4-fluoro-N-methylbenzamide (175 mg, 61.0 %) as a beige solid. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=C(C(=CN=C1Cl)Cl)I, amount is: 0.003650000086054206 MOLE;amine:CNC(=O)C1=C(C=C(C=C1)F)N, amount is: 0.0034799999557435513 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.006949999835342169 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.00020900000527035445 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.00013899999612476677 MOLE.Products are 0:CNC(=O)C1=C(C=C(C=C1)F)NC2=CC(=NC=C2Cl)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: palladium acetate (31.2 mg, 0.14 mmol) was added to 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (121 mg, 0.21 mmol), Cesium carbonate (2266 mg, 6.95 mmol), 2-amino-4-fluoro-N-methylbenzamide (585 mg, 3.48 mmol) and 2,5-dichloro-4-iodopyridine (1000 mg, 3.65 mmol) in dioxane (40 mL) under nitrogen. The resulting suspension was stirred at 80 °C for 18hrs then cooled. Product and bis product suggested. Disappointing! The reaction mixture was evaporated to dryness and redissolved in EtOAc (150 mL), and washed sequentially with saturated NaHCO3 (2 x 100 mL), water (100 mL), and saturated brine (100 mL). The organic layer was dried over MgSO4, filtered then evaporated. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford desired product as a yellow solid. |
Here is a chemical reaction formula: Reactants are amine:CC(=O)N1CC2CNCC(C1)O2, amount is: 0.00021300000662449747 MOLE;aryl halide:COC1=C(C=C(C=C1)Br)[N+](=O)[O-], amount is: 0.0001939999929163605 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.000291000003926456 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 1.5499999790336005e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 1.5499999790336005e-05 MOLE.Products are 0:CC(=O)N1CC2CN(CC(C1)O2)C3=CC(=C(C=C3)OC)[N+](=O)[O-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1-(9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl)ethanone (36.3 mg, 0.21 mmol), 4-bromo-1-methoxy-2-nitrobenzene (45 mg, 0.19 mmol), diacetoxypalladium (3.48 mg, 0.02 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (8.98 mg, 0.02 mmol) and sodium 2-methylpropan-2-olate (28.0 mg, 0.29 mmol) in dioxane (0.5 mL) were degassed with nitrogen and stirred at 110 °C for 4 hours => _some product formed, by-products are major + degradation_ **_ABANDONED_** |
Here is a chemical reaction formula: Reactants are amine:CC(C)(C)OC(=O)N1CCNCC1, amount is: 0.0033499998971819878 MOLE;aryl halide:CS(=O)(=O)C1=CC=C(C=C1)COC2=NC=C(C=N2)Br, amount is: 0.003000000026077032 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.004730000160634518 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.0001610000035725534 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.00016900000628083944 MOLE.Products are 0:CC(C)(C)OC(=O)N1CCN(CC1)C2=CN=C(N=C2)OCC3=CC=C(C=C3)S(=O)(=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 5-bromo-2-(4-(methylsulfonyl)benzyloxy)pyrimidine (1.03 g, 3.00 mmol), tert- butyl piperazine-1-carboxylate (624.6 mg, 3.35 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (154.3 mg, 0.17 mmol),2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (100.0 mg, 0.16 mmol) and sodium 2-methylpropan-2-olate (454.4 mg, 4.73 mmol) were mixed with toluene (20 mL). N2 was bubbled through the solvent for 15 minutes.The resulting mixture was stirred at 80 °C for over night under N2.The reaction mixture was filtered through celite. The reaction mixture was evaporated to dryness and redissolved in EtOAc (75 mL), and washed sequentially with water (2x75 mL) and saturated brine (100 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford tert-butyl 4-(2-(4-(methylsulfonyl)benzyloxy)pyrimidin-5-yl)piperazine-1-carboxylate (1.664 %) as a white solid. The product was not pure! The crude product was purified by flash alumina chromatography, elution gradient 0 to 70% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford tert-butyl 4-(2-(4-(methylsulfonyl)benzyloxy)pyrimidin-5-yl)piperazine-1-carboxylate (1.664 %) as a white solid. The product was still not pure but was handed in for testing anyway, as 92% pure by NMR. |
Here is a chemical reaction formula: Reactants are aryl halide:CS(=O)(=O)C1=CC=C(C=C1)COC2=NC=C(C=N2)Br, amount is: 0.0021800000686198473 MOLE;amine:CC(C)(C)OC(=O)N1CCNCC1, amount is: 0.002400000113993883 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.003269999986514449 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.00010900000052060932 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.00010900000052060932 MOLE.Products are 0:CC(C)(C)OC(=O)N1CCN(CC1)C2=CN=C(N=C2)OCC3=CC=C(C=C3)S(=O)(=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 5-bromo-2-(4-(methylsulfonyl)benzyloxy)pyrimidine (748.8 mg, 2.18 mmol), tert- butyl piperazine-1-carboxylate (447 mg, 2.40 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (100 mg, 0.11 mmol),2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (67.9 mg, 0.11 mmol) and sodium 2-methylpropan-2-olate (315 mg, 3.27 mmol) were mixed with toluene (20 mL). N2 was bubbled through the solvent for 15 minutes.The resulting mixture was stirred at 80 °C for over night under N2.The reaction mixture was filtered through celite. The reaction mixture was evaporated to dryness and redissolved in EtOAc (75 mL), and washed sequentially with water (2x75 mL) and saturated brine (100 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford tert-butyl 4-(2-(4-(methylsulfonyl)benzyloxy)pyrimidin-5-yl)piperazine-1-carboxylate (55.0 %) as a yellow solid. Was not pure and tailed on the coloumn. The crude product was purified by preparative HPLC (Phenomenex Gemini C18 110A (axia) column, 5µ silica, 21 mm diameter, 150 mm length), using decreasingly polar mixtures of water (containing 0.5% NH3 and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford as a white solid. The product crashed out on the HPLC coloumn and blocked the system, which gave bad recovery. Turns out the product is not stable. 2D TLC shows tailing of product.. |
Here is a chemical reaction formula: Reactants are aryl halide:CS(=O)(=O)C1=CC=C(C=C1)COC2=NC=C(C=C2)Br, amount is: 0.0007539999787695706 MOLE;amine:CC(C)(C)OC(=O)N1CCNCC1, amount is: 0.0008640000014565885 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0012499999720603228 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 7.760000153211877e-05 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 5.579999924520962e-05 MOLE.Products are 0:CC(C)(C)OC(=O)N1CCN(CC1)C2=CN=C(C=C2)OCC3=CC=C(C=C3)S(=O)(=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (48.3 mg, 0.08 mmol) was added in one portion to 5-bromo-2-(4-(methylsulfonyl)benzyloxy)pyridine (257.9 mg, 0.75 mmol), tert-butyl piperazine-1-carboxylate (160.9 mg, 0.86 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (51.1 mg, 0.06 mmol) and sodium 2-methylpropan-2-olate (120.1 mg, 1.25 mmol) in toluene (10 mL). N2 was bubbled through the solvent for 15 minutes.The resulting mixture was stirred at 80 °C for over night under N2.The reaction mixture was filtered through celite. The reaction mixture was evaporated to dryness and redissolved in EtOAc (75 mL), and washed sequentially with water (2x75 mL) and saturated brine (100 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 70% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford tert-butyl 4-(6-(4-(methylsulfonyl)benzyloxy)pyridin-3-yl)piperazine-1-carboxylate (42.6 %) as a yellow solid. |
Here is a chemical reaction formula: Reactants are aryl halide:CCOC(=O)C1=CC2=C(O1)C(=CC=C2)Br, amount is: 0.0017099999822676182 MOLE;amine:CC(=O)N1CCC2=C1C=CC(=C2)CCN3CCNCC3, amount is: 0.0017900000093504786 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.002219999907538295 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C, amount is: 0.00017100000695791095 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 8.550000347895548e-05 MOLE.Products are 0:CCOC(=O)C1=CC2=C(O1)C(=CC=C2)N3CCN(CC3)CCC4=CC5=C(C=C4)N(CC5)C(=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 06/05 2009 14:53:56 +0200 To ethyl 7-bromobenzofuran-2-carboxylate (0.460 g, 1.71 mmol) and 1-(5-(2-(piperazin-1-yl)ethyl)indolin-1-yl)ethanone (0.491 g, 1.79 mmol) (from EN02198-74) in dry degassed dioxane (8 mL) were added Cesium carbonate (0.724 g, 2.22 mmol), 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.081 g, 0.17 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (0.078 g, 0.09 mmol) under argon and the reaction heated at 95°C overnight. After cooling to rt, water and DCM were added and the layers separated. The aq phase was extracted with DCM (3x). The combined org phases were washed with water, dried (MgSO4), filtered and evaporated. The crude was purified by flash (SiO2; DCM/MeOH 95/5) to give 0.485 g (61%) of the product as a yellow solid. |
Here is a chemical reaction formula: Reactants are aryl halide:CCOC(=O)C1=CC2=C(O1)C(=CC=C2)Br, amount is: 0.0003530000103637576 MOLE;amine:CC(=O)N1CCC2=C1C=CC(=C2)CCN3CCNCC3, amount is: 0.000371000001905486 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.00045900000259280205 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C, amount is: 3.529999958118424e-05 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 1.7700000171316788e-05 MOLE.Products are 0:CCOC(=O)C1=CC2=C(O1)C(=CC=C2)N3CCN(CC3)CCC4=CC5=C(C=C4)N(CC5)C(=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 22/04 2009 09:43:42 +0200 To ethyl 7-bromobenzofuran-2-carboxylate (0.095 g, 0.35 mmol) and 1-(5-(2-(piperazin-1-yl)ethyl)indolin-1-yl)ethanone (0.101 g, 0.37 mmol) (from EN02198-74) in dry degassed dioxane (1.5 mL) were added Cesium carbonate (0.150 g, 0.46 mmol), 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.017 g, 0.04 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (0.016 g, 0.02 mmol) under argon and the reaction heated at 95°C for 5.5h. After cooling to rt, water and DCM were added and the layers separated. The aq phase was extracted with DCM (3x). The combined org phases were washed with water, dried (MgSO4), filtered and evaporated. The crude was purified by flash (SiO2; DCM/MeOH 95/5) to give 0.105 g of the product as a yellow solid. |
Here is a chemical reaction formula: Reactants are aryl halide:CCOC(=O)C1=CC2=C(O1)C(=CC=C2)Br, amount is: 0.008550000376999378 MOLE;amine:C1CN(CCN1)CCC2=CC=CC=N2, amount is: 0.009399999864399433 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.011099999770522118 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C, amount is: 0.0008549999911338091 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.00042699999175965786 MOLE.Products are 0:CCOC(=O)C1=CC2=C(O1)C(=CC=C2)N3CCN(CC3)CCC4=CC=CC=N4, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 27/05 2009 13:35:19 +0200 To dry degassed dioxane (30 mL) were added ethyl 7-bromobenzofuran-2-carboxylate (2.30 g, 8.55 mmol) and 1-(2-(pyridin-2-yl)ethyl)piperazine (1.798 g, 9.40 mmol), Cesium carbonate (3.62 g, 11.11 mmol), 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.407 g, 0.85 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (0.391 g, 0.43 mmol) under argon and the reaction heated at 95°C for 4h. The reaction mixture was filtered and solvent evaporated. The material was purified by flash (SiO2; DCM/MeOH 97/3) to give 0.620 g, but it was not pure enough (EN02198-94-001). A second flash was performed (SiO2; DCM/MeOH 97/3) to give 0.540 g of the product as a yellow solid (EN02198-94-002). 100% pure according to HPLC. The reaction mixture was combined with the reaction mixture in EN02745-56 and hydrolysed. |
Here is a chemical reaction formula: Reactants are aryl halide:CCOC(=O)C1=CC2=C(O1)C(=CC=C2)Br, amount is: 0.007430000230669975 MOLE;amine:C1CN(CCN1)CCC2=CC=CC=N2, amount is: 0.008179999887943268 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.011099999770522118 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C, amount is: 0.0010400000028312206 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.0005200000014156103 MOLE.Products are 0:CCOC(=O)C1=CC2=C(O1)C(=CC=C2)N3CCN(CC3)CCC4=CC=CC=N4, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The reaction mixture of ethyl 7-bromobenzofuran-2-carboxylate (2.0 g, 7.43 mmol), 1-(2-(pyridin-2-yl)ethyl)piperazine (1.564 g, 8.18 mmol), Tris(dibenzylideneacetone)dipalladium(0) (0.476 g, 0.52 mmol), 2-Dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl (0.496 g, 1.04 mmol) and Cesium carbonate (3.63 g, 11.15 mmol) in dioxane (30 mL) (degassed with argon for 10 min) was heated at 95 °C under argon for 5 h. After cooling, the reaction mixture was filtered and concentrated. The product was purified twice by isco, the first using DCM:MeOH (0-5%) and the second time using DCM:MeOH (0-3%). |
Here is a chemical reaction formula: Reactants are amine:C1CN(CCN1)CCC2=CC=CC=N2, amount is: 0.00039000000106170774 MOLE;aryl halide:CCOC(=O)C1=CC2=C(O1)C(=CC=C2)Br, amount is: 0.00037200000951997936 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0004830000107176602 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C, amount is: 3.719999949680641e-05 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 1.8599999748403206e-05 MOLE.Products are 0:CCOC(=O)C1=CC2=C(O1)C(=CC=C2)N3CCN(CC3)CCC4=CC=CC=N4, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 07/01 2009 12:44:11 +0100 To ethyl 7-bromobenzofuran-2-carboxylate (0.100 g, 0.37 mmol) and 1-(2-(pyridin-2-yl)ethyl)piperazine (0.075 g, 0.39 mmol) in dry degassed dioxane (1.5 mL) were added Cesium carbonate (0.157 g, 0.48 mmol), 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.018 g, 0.04 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (0.017 g, 0.02 mmol) under argon and the reaction heated at 95°C o/n. All starting material consumed. Water and DCM were added and the layers separated. The aq phase was extracted with DCM (3x). The combined org phases were washed with water, dried (MgSO4), filtered and evaporated. The crude was purified by flash (SiO2; DCM/MeOH 95/5) to give 0.0661 g of the product as a pale yellow semisolid. |
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