2-Methoxybenzoic acid → HCID 57855682, compound

Participants

Reaction Steps

DIPEA (149.8 mg, 1.16 mmol) was added at room temperature to a stirred solution of 2-methoxy-benzoic acid (39.2 mg, 0.26 mmol) in DMF (3 mL), HOBt (38.2 mg, 0.28 mmol) and EDCI.HCl (123 mg, 0.64 mmol). After 2 minutes biphenyl-4-carboxylic acid (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 50% EtOAc in hexane as eluent) to afford 60 mg (93.0% yield) of biphenyl-4-carboxylicacid {2-[4-(2-methoxy-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide. LC-MS purity: 92.98%, HPLC Purity: 98.70%. 1H NMR: (CDCl3) δ 7.94 (d, 2H), 7.7-7.6 (q, 4H), 7.52-7.44 (t, 2H), 7.44-7.4 (m, 1H), 7.4-7.3 (m, 2H), 7.1-7.0 (t, 1H), 7.0-6.92 (dd, 1H), 4.4-4.24 (dd, 2H), 4.0 (s, 1H), 3.88 (d, 3H), 3.8 (s, 2H), 3.7-3.58 (m, 2H), 3.5-3.24 (m, 3H).

Provenance & Evidence