2-(4-aminophenyl)-N-[2-(dimethylamino)ethyl]acetamide

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

Procedure: 2-(4-Aminophenyl)-N-[2-(dimethylamino)ethyl]acetamide (221 mg), WSC (free form: 0.23 ml), 1-hydroxybenzotriazole (199 mg), and dimethylaminopyridine (244 mg) were added to a DMF (5 ml) solution of 4-nitrophenylacetic acid (181 mg), which was stirred for 4 hours. The reaction mixture was poured into water, and extraction was conducted using ethyl acetate. The organic layer was washed with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution, dried over sodium sulfate, and then concentrated. The residue was recrystallized from methanol, to give the titled compound (80 mg). The organic layer was washed with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution dried over sodium sulfate concentrated The residue was recrystallized from methanol

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

Procedure: 2-(4-Aminophenyl)-N-[2-(dimethylamino)ethyl]acetamide (221 mg), WSC (249 mg), 1-hydroxybenzotrizole (199 mg), triethylamine (0.4 ml), and dimethylaminopyridine (244 mg) were added to a DMF (5 ml) solution of 3-[3-(2-naphthyl)-1,2,4-oxadiazol-5-yl]propionic acid (268 mg), which was stirred for 5 hours. The reaction mixture was poured into water, and extraction was conducted using ethyl acetate. The organic layer was washed with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution, dried over sodium sulfate, and then concentrated. The residue was recrystallized from methanol, to give the titled compound (166 mg). The organic layer was washed with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution dried over sodium sulfate concentrated The residue was recrystallized from methanol

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

Procedure: 2-(4-Aminophenyl)-N-[2-(dimethylamino)ethyl]acetamide (221 mg), WSC (249 mg), 1-hydroxybenzotriazole (199 mg), triethylamine (0.4 ml), and dimethylaminopyridine (244 mg) were added to a tetrahydrofuran (10 ml) solution of 1-[(benzyloxy)carbonyl]-4-piperidinecarboxylic acid (290 mg), which was stirred for 20 hours. The reaction mixture was poured into water, and extraction was conducted using ethyl acetate. The organic layer was washed with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution, dried over sodium sulfate, and then concentrated. The residue was recrystallized from methanol-diisopropyl ether, to give the titled compound (230 mg). The organic layer was washed with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution dried over sodium sulfate concentrated The residue was recrystallized from methanol-diisopropyl ether

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

Procedure: Pd-C (1 g) was added to a methanol (140 ml) solution of benzyl 4-[2-[[2-(dimethylamino)ethyl]amino]-2-oxoethyl]phenylcarbamate (10 g), which was stirred under hydrogen atmosphere for 1 hour. Pd-C was removed, and the filtrate was concentrated. The residue was purified by alumina column chromatography (development solvent; ethyl acetate:hexane=1:1), to give the titled compound (6.63 g) as an oily substance. Pd-C was removed the filtrate was concentrated The residue was purified by alumina column chromatography (development solvent; ethyl acetate:hexane=1:1)