2-Acetylbenzoic acid → HCID 66953526, compound

Participants

Reaction Steps

DIPEA (179.8 mg, 1.39 mmol) was added to the stirred solution of 2-acetyl-benzoic acid (50.75 mg, 0.31 mmol) in DMF (3 mL), HOBt (45.95 mg, 0.34 mmol) and EDCI.HCl (148.14 mg, 0.77 mmol) at room temperature. After 2 minutes biphenyl-4-carboxylicacid (2-oxo-2-piperazin-1-yl-ethyl)-amide (120 mg, 0.37 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 50% EtOAc in hexane as eluent) to afford 30 mg (20.6% yield) of biphenyl-4-carboxylicacid {2-[4-(2-acetyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide, LC-MS purity: 95.52%, 1H NMR: (DMSO) δ 8.64 (s, 1H), 8.0 (dd, 3H), 7.84-7.72 (q, 4H), 7.7-7.64 (t, 1H), 7.6 (t, 1H), 7.5 (t, 2H), 7.44-7.32 (m, 2H), 4.26-4.1 (dd, 2H), 3.76-3.62 (d, 4H), 3.46 (s, 2H), 3.3 (d, 2H), 2.6 (s, 3H).

Provenance & Evidence