1-Hydroxybenzotriazole → 5-Phenyl-pyridine-2-carboxylic acid {2-oxo-2-[4-(2-chloro-phenoxy)-piperidin-1-yl]-ethyl}-amide

Participants

Reaction Steps

To a stirred solution of [(5-phenyl-pyridine-2-carbonyl)-amino]-acetic acid (0.07 g, 0.00027 mol) in DMF (1.5 mL) was added DIPEA (0.105 g, 0.00082 mol), HOBt (0.044 g, 0.00033 mol) and EDCI.HCl (0.062 g, 0.00033 mol) at ambient temperature. After 2 minutes 4-(2-chlorophenoxy)piperidine hydrochloride (0.081 g, 0.000327 mol) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water and the product was extracted with ethyl acetate. The ethyl acetate layer was washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure to afford 0.0545 g (44%) of 5-phenyl-pyridine-2-carboxylic acid {2-oxo-2-[4-(2-chloro-phenoxy)-piperidin-1-yl]-ethyl}-amide. LCMS: 484.18 (M+1)+, 95.40%, 1H NMR (DMSO-d6): δ 9.0 (d, 1H), 8.8 (t, 1H), 8.3 (dd, 1H), 8.1 (d, 1H), 7.8 (d, 1H), 7.6-7.4 (m, 2H), 7.3-7.2 (m, 2H), 7.0-6.9 (m, 1H), 4.8-4.7 (m, 1H), 4.3 (d, 1H), 3.8-3.6 (m, 2H), 3.5 (m, 2H), 2.0-1.9 (m, 2H), 1.8-1.6 (m, 2H).

Provenance & Evidence