ethyl 2-(2-carbamoylanilino)acetate

反応条件: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 2 g of ortho-aminobenzamide were added 4.04 g (2 equivalents) of potassium carbonate, 4.94 g (2 equivalents) of ethyl bromoacetate, and the mixture was stirred under heating at 160° C. for 3 hours. After cooling to room temperature, water was added and the mixture extracted with ethyl acetate. After washing with aqueous sodium chloride, the mixture was dried over anhydrous magnesium sulfate, followed by evaporation of the solvent. The residue was developed with hexaneethyl acetate (1:2) by silica gel column chromatography to obtain 760 mg of the desired compound (yield 23.3%). After cooling to room temperature the mixture extracted with ethyl acetate After washing with aqueous sodium chloride the mixture was dried over anhydrous magnesium sulfate followed by evaporation of the solvent

反応条件: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 2 g of ortho-aminobenzamide were added 4.04 g (2 equivalents) of potassium carbonate, 4.94 g (2 equivalents) of ethyl bromoacetate, and the mixture was stirred under heating at 160° C. for 3 hours. After cooling to room temperature, water was added and the mixture extracted with ethyl acetate. After washing with aqueous sodium chloride, the mixture was dried over anhydrous magnesium sulfate, followed by evaporation of the solvent. The residue was developed with hexaneethyl acetate (1:2) by silica gel column chromatography to obtain 760 mg of the desired compound (yield 23.3%). After cooling to room temperature the mixture extracted with ethyl acetate After washing with aqueous sodium chloride the mixture was dried over anhydrous magnesium sulfate followed by evaporation of the solvent

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2-aminobenzamide (100 g), ethyl bromoacetate (97.74 ml) and potassium carbonate (253.78 g) in N,N-dimethylformamide (400 ml) was stirred at 60° C. for 4.5 hours. After cooling, the reaction mixture was poured into ice-water (2 l) and the resulting crystals were collected by filtration. Thus obtained product was purified by recrystallization from ethanol to give ethyl N-(2-carbamoylphenyl)aminoacetate (123.93 g). After cooling the resulting crystals were collected by filtration Thus obtained product was purified by recrystallization from ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 3-(2,3-difluorophenyl)-propionic acid (Int. A1) (5 g, 26.9 mmol) in anhydrous dichloromethane (50 ml) containing a few drops of DMF was added oxalyl chloride (4.7 ml, 53.8 mmol) at 0° C. under argon. The solution was then stirred at ambient temperature for 2 h and the solvent removed in vacuo. The residue which contained the acid chloride (Int. A54) was dissoved in toluene (50 ml) and added to a slurry of (2-carbamoylphenylamino)-acetic acid ethyl ester (5.0 g, 22.5 mmol) in toluene (50 ml) containing pyridine (1 ml) and 4-dimethylaminopyridine (DMAP) (100 mg). After 16 h at 90° C. the solvent was evaporated and the solid residue washed with water, aqueous ammonia and ether to give the title compound (6.9 g, 82%) as a cream solid. 1H-NMR (DMSO) δ 1.24 (3H, t), 3.13 (2H, t), 3.34 (2H, m), 4.24 (2H, q), 5.48 (2H, s), 7.19 (1H, m), 7.29-7.35 (2H, m), 7.60-7.72 (2H, m), 7.94 (1H, t), 8.19 (1H, d); MS (APCI+) found (M+1)=373; C20H18F2N2O3 requires 372. the solvent removed in vacuo After 16 h at 90° C. the solvent was evaporated the solid residue washed with water, aqueous ammonia and ether

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2-aminobenzamide (100 g), ethyl bromoacetate (97.74 ml) and potassium carbonate (253.78 g) in N,N-dimethylformamide (400 ml) was stirred at 60° C. for 4.5 hours. After cooling, the reaction mixture was poured into ice-water (2 l) and the resulting crystals were collected by filtration. Thus obtained product was purified by recrystallization from ethanol to give ethyl N-(2-carbamoylphenyl)aminoacetate (123.93 g). After cooling the resulting crystals were collected by filtration Thus obtained product was purified by recrystallization from ethanol

反応条件: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 2 g of ortho-aminobenzamide were added 4.04 g (2 equivalents) of potassium carbonate, 4.94 g (2 equivalents) of ethyl bromoacetate, and the mixture was stirred under heating at 160° C. for 3 hours. After cooling to room temperature, water was added and the mixture extracted with ethyl acetate. After washing with aqueous sodium chloride, the mixture was dried over anhydrous magnesium sulfate, followed by evaporation of the solvent. The residue was developed with hexaneethyl acetate (1:2) by silica gel column chromatography to obtain 760 mg of the desired compound (yield 23.3%). After cooling to room temperature the mixture extracted with ethyl acetate After washing with aqueous sodium chloride the mixture was dried over anhydrous magnesium sulfate followed by evaporation of the solvent

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2-aminobenzamide (100 g), ethyl bromoacetate (97.74 ml) and potassium carbonate (253.78 g) in N,N-dimethylformamide (400 ml) was stirred at 60° C. for 4.5 hours. After cooling, the reaction mixture was poured into ice-water (2 l) and the resulting crystals were collected by filtration. Thus obtained product was purified by recrystallization from ethanol to give ethyl N-(2-carbamoylphenyl)aminoacetate (123.93 g). After cooling the resulting crystals were collected by filtration Thus obtained product was purified by recrystallization from ethanol