1,2-Dichloroethane → N-(3-(azepan-1-yl)propyl)-1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)-N-methylpiperidine-4-carboxamide

Participants

Reaction Steps

To a solution of 1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid (A-3, 70 mg, 0.52 mmole), 3-(azepan-1-yl)-N-methylpropan-1-amine (20 mg) and DIPEA (0.05 mL) in DMF (2 mL) was added EDC (35 mg). The reaction solution was stirred at room temperature for 12 hours. The reaction was diluted with EtOAc (30 mL). The organic layer was washed with saturated sodium bicarbonate (10 mL), water (10 mL) and dried over anhydrous magnesium sulfate. After filtration and concentration, the residue was purified through chromatography (CH2Cl2:MeOH 10:1) to give N-(3-(azepan-1-yl)propyl)-1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)-N-methylpiperidine-4-carboxamide (42 mg, 82%). H1NMR (300 MHz, CDCl3), ppm: 7.97 (d, 2H), 7.48 (d, 2H), 3.80 (m, 1H), 3.63 (m, 2H), 3.45 (m, 2H), 3.31-3.14 (m, 7H), 2.75 (s, 3H), 2.44 (m, 4H), 2.01 (m, 2H), 1.85 (m, 10H), 1.30 (m, 2H), 1.26 (m, 2H). MS (ESI+) M/z: 487, 489 (M+H).

Provenance & Evidence