2-Chlorobenzoic Acid → HCID 57855658, compound

Participants

Reaction Steps

DIPEA (149.8 mg, 1.15 mmol) was added to a stirred solution of 2-chloro-benzoic acid (40.3 mg, 0.26 mmol) in DMF (3 mL), HOBt (38.2 mg, 0.28 mmol) and EDCI.HCl (123.4 mg, 0.64 mmol) at room temperature. After 2 minutes biphenyl-4-carboxylicacid (2-oxo-2-piperazin-1-yl-ethyl)-amide (100 mg, 0.31 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added, and the resulting precipitate was filtered. The residue was purified by column chromatography (using 60-120 mesh silica gel and 60% EtOAc in hexane as eluent) to afford 46 mg (38.6% yield) of biphenyl-4-carboxylicacid {2-[4-(2-chloro-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide, LC-MS purity: 99.47%, 1H NMR: (DMSO) δ 8.7-8.6 (bs, 1H), 8.02-7.92 (d, 2H), 7.84-7.7 (q, 4H), 7.6-7.38 (m, 7H), 4.24 (d, 1H), 4.18 (d, 1H), 3.8-3.6 (m, 4H), 3.56-3.46 (m, 2H), 3.26-3.12 (m, 2H).

Provenance & Evidence