Benzoic Acid → 4-[1,3,4]oxadiazol-2-yl-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide

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Reaction Steps

DIPEA (154 mg, 0.2 mL, 1.19 mmol) was added drop wise to 4-[1,3,4]oxadiazol-2-yl)-benzoic acid (65 mg, 0.34 mmol) in DMF (3 mL). EDCI (98.2 mg, 0.51 mmol) and HOBT (50 mg, 0.37 mmol) were then added. After 2 minutes, 2-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone in its HCl salt form (150 mg, 0.4 mmol) was added. The resulting mixture was stirred at room temperature overnight. Cold water was then added and filtered the solid precipitated to afford 90 mg (54% yield) of 4-[1,3,4]oxadiazol-2-yl-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide. LCMS Purity: 94.4%. 1H NMR (DMSO-d6): δ 9.4 (s, 1H), 8.9 (bs, 1H), 8.5 (s, 1H), 8.15 (dd, 2H), 7.7 (m, 4H), 7.55 (t, 1H), 4.2 (dd, 2H), 3.7 (bs, 4H), 3.5 (s, 1H), 3.1 (d, 3H).

Provenance & Evidence