1-Hydroxybenzotriazole → 3-oxo-N-(6-phenyl-pyridin-3-yl)-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionamide

Participants

Reaction Conditions

Reaction Steps

HOBt (48 mg, 0.35 mmol) and DMAP (54 mg, 0.44 mmol) were added to a stirred solution of 3-oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acid (100 mg, 0.29 mmol) in DMF (2 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (67 mg, 0.35 mmol) followed by 6-phenyl-pyridin-3-ylamine (50 mg, 0.29 mmol) were added. The reaction mixture was stirred at the room temperature overnight then diluted with water and the product extracted with ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated. The residue was purified by column chromatography using silica gel 60-120 mesh (60% ethyl acetate in hexane) to afford 36 mg (25%) of 3-oxo-N-(6-phenyl-pyridin-3-yl)-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionamide. LCMS: 497.16 (M+1)+, 97.8%, 1H NMR: (CDCl3): δ 10.0 (d, 1H), 8.7 (d, 1H), 8.2 (dd, 1H), 8.0 (d, 2H), 7.7 (m, 4H), 7.4 (m, 4H), 4.03 (m, 2H), 3.7 (m, 3H), 3.54 (m, 3H), 3.23 (m. 2H).

Provenance & Evidence