1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 25166303, compound

Participants

Reaction Steps

DIPEA (143 mg, 0.193 mL, 1.11 mmol) was added to a stirred solution of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (prepared by the method described above) (157 mg, 0.44 mmol) in DMF (2 mL). HOBT (60 mg, 0.44 mmol) and EDCI (85 mg, 0.44 mmol) were then added at room temperature. After 2 minutes, 1H-Indole-3-carboxylic acid (60 mg, 0.37 mmol) was added and the resulting mixture was stirred at room temperature for 4 hrs. 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 the residue. The residue was purified by preparative HPLC to afford 21.3 mg (12.35% yield) of 1H-Indole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 95.81%. 1H NMR (CDCl3): δ 9.1 (s, 1H), 8.1 (d, 1H), 7.9-7.5 (m, 4H), 7.4-7.1 (m, 4H), 4.4-4.2 (m, 2H), 4.1-3.8 (m, 2H), 3.8-3.4 (m, 4H), 3.4-3.1 (m, 3H).

Provenance & Evidence