1-Hydroxybenzotriazole → HCID 44235274, compound

Participants

Reaction Steps

To a stirred solution of [(biphenyl-4-carbonyl)-amino]-acetic acid (0.1 g, 0.00039 mol) in DMF (2 mL), was added DIPEA (0.2025 g, 0.00156 mol), HOBt (0.053 g, 0.00039 mol) and EDCI.HCl (0.0901 g, 0.00047 mol) at ambient temperature. After 2 minutes (2-bromo-phenyl)-methyl-piperidin-4-yl-amine hydrochloride (0.119 g, 0.00039 mol) was added and the resulting mixture was stirred at the same temperature overnight. The reaction mixture was diluted with cold water, and the resulting precipitate was isolated by filtration. Purification by preparative TLC using 30% ethyl acetate in hexane afforded 0.072 g (36%) of biphenyl-4-carboxylic acid (2-{4-[(2-bromo-phenyl)-methyl-amino]-piperidin-1-yl}-2-oxo-ethyl)-amide. LCMS: 506.1 (M+1)+, 97.07%, 1H NMR (DMSO-d6): δ 8.6 (t, 1H), 8.0 (d, 2H), 7.8 (d, 2H), 7.75 (m, 4H), 7.6-7.25 (m, 6H), 7.0 (t, 1H), 4.4 (m, 1H), 4.2 (m, 1H), 3.9 (m, 1H), 3.05 (m, 1H), 2.7 (m, 1H), 2.6 (s, 3H), 1.8-1.5 (m, 4H).

Provenance & Evidence