Phenylacetic Acid → HCID 25164322, compound

Participants

Reaction Steps

DIPEA (68 mg, 0.53 mmol) was added to a stirred solution of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone TFA salt (76 mg, 0.18 mmol) in DMF (1 mL). HOBT (24 mg, 0.18 mmol) and EDCI.HCl (34 mg, 0.18 mmol) were then added at room temperature. After 2 minutes, phenyl acetic acid (20 mg, 0.15 mmol) was added and the resulting mixture was stirred at room temperature for 4 hrs. Cold water (20 mL) was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure. the resulting residue was purified by column chromatography (using silica gel 60-120 mesh and 1% methanol in chloroform as eluent) to afford 28 mg (43.7% yield) of N-{2-Oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-2-phenyl-acetamide. LCMS Purity: 94.1%, 1H NMR (CDCl3): δ 7.8-7.7 (d, 1H). 7.6 (m, 2H), 7.4-7.2 (m, 5H), 6.5 (bd, 1H), 4.1 (m, 1H), 4.0 (m, 2H), 3.8 (m, 1H), 3.8-3.4 (m, 6H), 3.3 (t, 1H), 3.2-3.1 (m, 2H).

Provenance & Evidence