1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 44231801, compound

Participants

Reaction Steps

DIPEA (453 mg, 3.51 mmol) was added to N-(5-phenyl-pyridin-2-yl)-malonamic acid (300 mg, 1.17 mmol), which was prepared following the synthetic route described in method II, in DMF (3 mL) followed by EDCI (336 mg, 1.75 mmol) and HOBT (189 mg, 1.4 mmol). After 2 minutes, piperazin-1-yl-(3,4,5-trifluoro-phenyl)-methanone hydrochloride (328 mg, 1.17 mmol) was added and stirring was continued at room temperature overnight. Cold water was then added and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. Purification by preparative HPLC afforded 85 mg (15% yield) of 3-oxo-N-(5-phenyl-pyridin-2-yl)-3-[4-(3,4,5-trifluoro-benzoyl)-piperazin-1-yl]-propionamide. LC/S [M+H]+: 483.16, 97.03%. 1H NMR (300 MHz, DMSO-d6): δ 10.7 (s, 1H), 8.7 (s, 1H), 8.1 (s, 2H), 7.7 (d, 2H), 7.5 (m, 4H), 7.4 (m, 1H), 3.7-3.1 (bs, 2H), 3.6-3.2 (m, 8H).

Provenance & Evidence