2-Methylbenzoic acid → N-Biphenyl-4-yl-3-[4-(2-methyl-benzoyl)-piperazin-1-yl]-3-oxo-propionamide

Participants

Reaction Conditions

Reaction Steps

HOBt (34 mg, 0.25 mmol) and DIPEA (67.9 mg, 0.51 mmol) were added to a stirred solution of 2-methyl-benzoic acid (29 mg, 0.21 mmol) in DMF (2 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (48 mg, 0.25 mmol) followed by N-biphenyl-4-yl-3-oxo-3-piperazin-1-yl-propionamide.hydrochloride (75 mg, 0.2 mmol) were added. The reaction mixture was stirred at room temperature overnight, then diluted with water. The resulting precipitate was filtered then purified by column chromatography using silica gel 60-120 mesh (80% ethyl acetate in hexane) to afford 23 mg (25%) of N-Biphenyl-4-yl-3-[4-(2-methyl-benzoyl)-piperazin-1-yl]-3-oxo-propionamide. LCMS: 442.21 (M+1)+, 95.7%. 1H NMR: (CDCl3): δ 9.6 (d, 1H), 7.6 (m, 6H), 7.42 (t, 2H), 7.32 (t, 2H), 7.22 (m, 1H), 7.16 (d, 1H), 3.8 (m, 4H), 3.5 (m, 4H), 3.3 (m, 2H).

Provenance & Evidence