5-Nitro-2-Furoic Acid → 5-Nitro-furan-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide

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Reaction Steps

DIPEA (50 mg, 0.38 mmol) was added to a stirred solution of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone-TFA salt (66 mg, 0.15 mmol) in DMF (1 mL). HOBT (21 mg, 0.15 mmol) and EDCI.HCl (29 mg, 0.15 mmol) were added at room temperature. After 2 minutes, 5-nitro-furan-2-carboxylic acid (20 mg, 0.13 mmol) was added. The resulting mixture was stirred at room temperature for four hours. Water was then added, and the product was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. Purification by column chromatography (using silica gel of mesh size of 60-120 and 3% methanol in chloroform as the eluent) afforded 28 mg (49.12% yield) of 5-nitro-furan-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 97.329%, HPLC Purity %: 95.234, 1H NMR (CDCl3): δ 7.8-7.7 (d, 1H), 7.7-7.5 (m, 3H), 7.4-7.3 (m, 2H), 4.4-4.3 (t, 1H), 4.2 (bt, 1H), 4.1-3.8 (m, 2H), 3.8-3.5 (m, 4H), 3.4 (bt, 1H), 3.3-3.2 (m, 2H).

Provenance & Evidence