methyl 3-anilinopropanoate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-methylamino-3-nitro-benzoic acid chloride (23.3 mmol) and 3-phenylamino-propionic acid methyl ester (23.3 mmol) in 80 mL dry tetrahydrofuran (THF) triethylamine (50.2 mmol) was added dropwise under stirring at room temperature. After three hours the reaction mixture was evaporated to dryness, the remaining solid triturated with water and the solid product isolated through filtration. After three hours the reaction mixture was evaporated to dryness the remaining solid triturated with water the solid product isolated through filtration

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-methylamino-3-nitro-benzoic acid chloride (23.3 mmol) and 3-phenylamino-propionic acid methyl ester (23.3 mmol) in 80 mL dry tetrahydrofuran (THF) triethylamine (50.2 mmol) was added dropwise under stirring at room temperature. After three hours the reaction mixture was evaporated to dryness, the remaining solid triturated with water and the solid product isolated through filtration. After three hours the reaction mixture was evaporated to dryness the remaining solid triturated with water the solid product isolated through filtration

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of 0.50 g (2.2 mmol) of 1-methyl-2-methoxymethylthieno[2,3-d]imidazol-5-yl-carboxylic acid in 20 mL of methylene chloride was mixed with 2.0 mL (3.2 g, 27 mmol) of thionyl chloride and refluxed for 60 minutes, during which time the solid gradually dissolved. After distillation of the liquid components, the crude product was taken up twice more in methylene chloride. After the solvent had been eliminated once more, the crude acid chloride was taken up in 20 mL of tetrahydrofuran and added dropwise to a mixture of 0.42 g (2.3 mmol) of N-(2-methoxycarbonylethyl)aniline and 0.92 mL (6.6 mmol) of triethylamine in 30 mL of tetrahydrofuran. After 16 hours stirring at 50° C., the solvent was eliminated and the crude product obtained was purified by chromatography (silica gel; methylene chloride/ethanol=100:1). Yield: 0.66 g (77% of theory); Rf value: 0.47 (silica gel; methylene chloride/ethanol=19:1). refluxed for 60 minutes, during which time the solid gradually dissolved After distillation of the liquid components

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 16.7 g (0.1 mol) of 4-nitrobenzoic acid were refluxed in 50 mL of thionyl chloride and 3 drops of dimethylformamide for 1 hour. After the solvent had been distilled off in vacuo, the crude product was dissolved in 150 mL of tetrahydrofuran and added dropwise to a solution of 18 g (0.1 mol) of N-(2-methoxycarbonylethyl)aniline in 250 mL of tetrahydrofuran and 42 mL (0.3 mol) of triethylamine. After being stirred for one hour at ambient temperature, the reaction mixture was diluted with 250 mL of ethyl acetate and washed 2× with 200 mL of 14% saline solution. After the solvent had been distilled off and the residue chromatographed (silica gel; methylene chloride), a yellow oil was obtained which slowly solidified. Yield: 32.6 g (100% of theory); Rf value: 0.37 (silica gel; methylene chloride/methanol=50:1). After the solvent had been distilled off in vacuo the crude product was dissolved in 150 mL of tetrahydrofuran washed 2× with 200 mL of 14% saline solution After the solvent had been distilled off the residue chromatographed (silica gel; methylene chloride) a yellow oil was obtained which

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.4 g (1.3 mmol) of 2-[2-(4-cyanophenyl)ethyl]quinazoline-7-carboxylic acid and 5 mL of thionyl chloride were stirred for 60 minutes at 50° C. Then the thionyl chloride was distilled off, the residue was dissolved in methylene chloride, mixed with 0.24 g (1.3 mmol) of methyl 3-(N-phenylamino)propionate and 0.22 mL of (1.3 mmol) of N-ethyldiisopropylamine and stirred for 18 hours at ambient temperature. After evaporation of the solvent in vacuo, the residue was chromatographed on silica gel and eluted with methylene chloride containing 1% methanol. Yield: 230 mg (37% of theory); Rf value: 0.64 (silica gel, methylene chloride/methanol=9:1). Then the thionyl chloride was distilled off the residue was dissolved in methylene chloride After evaporation of the solvent in vacuo the residue was chromatographed on silica gel eluted with methylene chloride containing 1% methanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of 0.50 g (2.2 mmol) of 1-methyl-2-methoxymethylthieno[2,3-d]imidazol-5-yl-carboxylic acid in 20 mL of methylene chloride was mixed with 2.0 mL (3.2 g, 27 mmol) of thionyl chloride and refluxed for 60 minutes, during which time the solid gradually dissolved. After distillation of the liquid components, the crude product was taken up twice more in methylene chloride. After the solvent had been eliminated once more, the crude acid chloride was taken up in 20 mL of tetrahydrofuran and added dropwise to a mixture of 0.42 g (2.3 mmol) of N-(2-methoxycarbonylethyl)aniline and 0.92 mL (6.6 mmol) of triethylamine in 30 mL of tetrahydrofuran. After 16 hours stirring at 50° C., the solvent was eliminated and the crude product obtained was purified by chromatography (silica gel; methylene chloride/ethanol=100:1). Yield: 0.66 g (77% of theory); Rf value: 0.47 (silica gel; methylene chloride/ethanol=19:1). refluxed for 60 minutes, during which time the solid gradually dissolved After distillation of the liquid components

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 16.7 g (0.1 mol) of 4-nitrobenzoic acid were refluxed in 50 mL of thionyl chloride and 3 drops of dimethylformamide for 1 hour. After the solvent had been distilled off in vacuo, the crude product was dissolved in 150 mL of tetrahydrofuran and added dropwise to a solution of 18 g (0.1 mol) of N-(2-methoxycarbonylethyl)aniline in 250 mL of tetrahydrofuran and 42 mL (0.3 mol) of triethylamine. After being stirred for one hour at ambient temperature, the reaction mixture was diluted with 250 mL of ethyl acetate and washed 2× with 200 mL of 14% saline solution. After the solvent had been distilled off and the residue chromatographed (silica gel; methylene chloride), a yellow oil was obtained which slowly solidified. Yield: 32.6 g (100% of theory); Rf value: 0.37 (silica gel; methylene chloride/methanol=50:1). After the solvent had been distilled off in vacuo the crude product was dissolved in 150 mL of tetrahydrofuran washed 2× with 200 mL of 14% saline solution After the solvent had been distilled off the residue chromatographed (silica gel; methylene chloride) a yellow oil was obtained which

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.4 g (1.3 mmol) of 2-[2-(4-cyanophenyl)ethyl]quinazoline-7-carboxylic acid and 5 mL of thionyl chloride were stirred for 60 minutes at 50° C. Then the thionyl chloride was distilled off, the residue was dissolved in methylene chloride, mixed with 0.24 g (1.3 mmol) of methyl 3-(N-phenylamino)propionate and 0.22 mL of (1.3 mmol) of N-ethyldiisopropylamine and stirred for 18 hours at ambient temperature. After evaporation of the solvent in vacuo, the residue was chromatographed on silica gel and eluted with methylene chloride containing 1% methanol. Yield: 230 mg (37% of theory); Rf value: 0.64 (silica gel, methylene chloride/methanol=9:1). Then the thionyl chloride was distilled off the residue was dissolved in methylene chloride After evaporation of the solvent in vacuo the residue was chromatographed on silica gel eluted with methylene chloride containing 1% methanol

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of 0.50 g (2.2 mmol) of 1-methyl-2-methoxymethyl-thieno[2.3-d]imidazol-5-yl-carboxylic acid in 20 ml of methylene chloride was mixed with 2.0 ml (3.2 g, 27 mmol) of thionyl chloride and refluxed for 60 minutes, during which time the solid gradually dissolved. After distillation of the liquid components the crude product was taken up twice more in methylene chloride. After the solvent had been eliminated once more the crude acid chloride was taken up in 20 ml of tetrahydrofuran and added dropwise to a mixture of 0.42 g (2.3 mmol) of N-(2-methoxycarbonylethyl)aniline and 0.92 ml (6.6 mmol) of triethylamine in 30 ml of tetrahydrofuran. After 16 hours' stirring at 50° C. the solvent was eliminated and the crude product obtained was purified by chromatography (silica gel; methylene chloride/ethanol=100:1). Yield: 0.66 g (77% of theory), Rf value: 0.47 (silica gel; methylene chloride/ethanol=19:1) refluxed for 60 minutes, during which time the solid gradually dissolved After distillation of the liquid components the crude product

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 16.7 g (0.1 mol) of 4-nitrobenzoic acid were refluxed in 50 ml of thionyl chloride and 3 drops of dimethylformamide for 1 hour. After the solvent had been distilled off in vacuo the crude product was dissolved in 150 ml of tetrahydrofuran and added dropwise to a solution of 18 g (0.1 mol) of N-(2-methoxycarbonylethyl)aniline in 250 ml of tetrahydrofuran and 42 ml 0.3 mol) of triethylamine. After being stirred for one hour at ambient temperature the reaction mixture was diluted with 250 ml of ethyl acetate and washed 2× with 200 ml of 14% saline solution. After the solvent had been distilled off and the residue chromatographed (silica gel; methylene chloride) a yellow oil was obtained which slowly solidified. Yield: 32.6 g (100% of theory), Rf value: 0.37 (silica gel; methylene chloride/methanol=50:1) After the solvent had been distilled off in vacuo the crude product was dissolved in 150 ml of tetrahydrofuran washed 2× with 200 ml of 14% saline solution After the solvent had been distilled off the residue chromatographed (silica gel; methylene chloride) a yellow oil was obtained which