1-Hydroxybenzotriazole → HCID 57855680, compound

Participants

Reaction Steps

DIPEA (149.8 mg, 1.16 mmol) was added to a stirred solution of 2-fluoro-5-trifluoromethyl-benzoic acid (53.6 mg, 0.26 mmol) in DMF (3 mL), HOBt (38.2 mg, 0.28 mmol) and EDCI.HCl (123 mg, 0.64 mmol) at room temperature. After 2 minutes Biphenyl-4-carboxylicacid (2-oxo-2-piperazin-1-yl-ethyl)-amide (100 mg, 0.309 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 56 mg (42.3% yield) of biphenyl-4-carboxylicacid {2-[4-(2-fluoro-5-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide. LC-MS purity: 99.19%, HPLC Purity: 98.21%. 1H NMR: (DMSO) δ 8.7 (t, 1H), 8.0-7.9 (d, 4H), 7.84-7.7 (q, 4H), 7.6 (t, 1H), 7.5 (t, 2H), 7.4 (t, 1H), 4.2 (dd, 2H), 3.8-3.6 (d, 4H), 3.6-3.4 (s, 2H), 3.3 (s, 2H).

Provenance & Evidence