Diisopropylethylamine → Biphenyl-4-carboxylic acid {2-[4-(2-bromo-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide

Participants

Reaction Steps

To a stirred solution of [(biphenyl-4-carbonyl)-amino]-acetic acid (0.075 g, 0.00029 mol) in DMF (2 mL), was added DIPEA (0.1139 g, 0.00088 mol) HOBt (0.0398 g, 0.00029 mol) and EDCI.HCl (0.06758 g, 0.00035 mol) at ambient temperature. After 2 minutes (2-bromo-phenyl)-piperidin-4-yl-amine dihydrochloride (0.09639 g, 0.00029 mol) was added and the resulting mixture was stirred at the same temperature for overnight. The reaction mixture was diluted with cold water and the resulting precipitate was isolated by filtration, washed with hexane followed by ether and dried to afford 0.067 g (46%) of biphenyl-4-carboxylic acid {2-[4-(2-bromo-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 492.0 (M+1)+, 90.08%, 1H NMR (DMSO-d6): δ 8.62 (t, 1H), 7.94 (d, 2H), 7.79 (m, 4H), 7.5 (t, 2H), 7.4 (t, 2H), 7.2 (t, 1H), 6.84 (d, 1H), 6.57 (d, 1H), 4.6 (d, 1H), 4.3 (d, 1H), 4.2 (d, 2H), 3.9 (d, 1H), 3.6 (d, 1H), 2.7 (t, 1H), 1.9 (bs, 2H), 1.5-1.2 (m, 3H).

Provenance & Evidence