1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178523544, compound

Participants

Reaction Steps

DIPEA (418 mg, 0.56 mL, 3.2 mmol) was added to a stirred solution of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (303.4 mg, 0.86 mmol) in DMF (4 mL). HOBT (106 mg, 0.79 mmol) and EDCI (344 mg, 1.7 mmol) were then added at room temperature. After 2 minutes, 6-hydroxy nicotinic acid (100 mg, 0.71 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water 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 to get the residue. The obtained residue was purified by preparative HPLC to afford 77 mg (24.6% yield) of 6-hydroxy-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-nicotinamide. LCMS Purity: 95.26%. 1H NMR (DMSO-d6): δ 12 (s, 1H), 8.4 (s, 1H), 7.9-7.74 (m, 3H), 7.72-7.62 (m, 1H), 7.6-7.5 (m, 1H), 4.2-4.0 (d, 2H), 3.9-3.52 (m, 5H), 3.24-3.0 (m, 3H).

Provenance & Evidence