Hydrochloric Acid → N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-6-phenylamino-nicotinamide

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Reaction Steps

DIPEA (126 mg, 0.17 mL, 0.98 mmol) was added drop wise to 6-(phenyl-amino)-pyridine-3-carboxylic acid (70 mg, 0.32 mmol) in DMF (5 mL). EDCI (74 mg, 0.39 mmol) and HOBT (53 mg, 0.39 mmol) were added consecutively and, after 10 minutes, 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone in its HCl salt form (137 mg, 0.39 mmol) was added. The resulting mixture was stirred at room temperature overnight. Cold water was then added and filtered the solid precipitated to afford 110 mg (65% yield) of N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-6-phenylamino-nicotinamide. LC-MS purity: 93.71%. 1H-NMR (DMSO-d6): δ 9.4 (s, 1H), 8.7 (s, 1H), 8.5 (t, 1H), 8.0 (d, 1H), 7.8 (m, 2H), 7.7 (d, 3H), 7.6 (m, 1H), 6.9 (t, 1H), 6.8 (d, 1H), 4.2 (dd, 2H), 3.6 (m, 4H), 3.4 (m, 2H), 3.2 (m, 2H).

Provenance & Evidence