Water → 2-[(5-Phenyl-isoxazol-3-ylmethyl)-amino]-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone

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Reaction Conditions

Reaction Steps

K2CO3 (201 mg, 1.46 mmol) was added to a stirred solution of methanesulfonic acid 5-phenyl-isoxazol-3-ylmethyl ester (200 mg, 0.73 mmol) and 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (257 mg, 0.73 mmol) in DMF (4 mL). The resulting mixture was heated at 40° C. for 1 hr. Cold water was then added and the resulting precipitate was isolated by filtration. The crude solid was purified by column chromatography using (silica gel of 60-120 mesh and 2% MeOH in CHCl3 as eluent) to afford 32 mg (9.2% yield) of 2-[(5-phenyl-isoxazol-3-ylmethyl)-amino]-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone. LCMS Purity: 96.53%. 1H NMR (DMSO-d6): δ 9.85 (s, 2H), 7.96-7.82 (m, 3H), 7.82-7.74 (t, 1H), 7.3 (d, 1H), 6.64-6.48 (d, 1H), 4.0-3.9 (d, 2H), 3.9-3.8 (m, 1H), 3.76-3.56 (m, 2H), 3.56-3.4 (m, 4H), 3.56-3.26 (bs, 1H), 3.2 (d, 2H), 2.49-2.29 (bs, 1H).

Provenance & Evidence