Triethylamine → HCID 67439459, compound

Participants

Reaction Conditions

Reaction Steps

Triethylamine (142 μL, 1.02 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (196 mg, 1.02 mmol), and 1-hydroxy-7-azabenzotriazole (139 mg, 1.02 mmol) were added to a solution of (2Z)-3-allyl-6-(2,3-difluorophenyl)azepan-2-one hydrazone (285 mg, 1.02 mmol) and 3,3,3-trifluoropropanoic acid (90 μL, 1.02 mmol) in acetonitrile (25 mL). After 18 h, additional triethylamine (0.14 mL, 1.02 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (100 mg, 0.52 mmol), 1-hydroxy-7-azabenzotriazole (70 mg, 0.51 mmol) and 3,3,3-trifluoropropanoic acid (45 μL, 0.51 mmol) were added. After 5.5 h, the reaction mixture was heated to 60° C. After 2.5 h, the mixture was cooled to ambient temperature. After 18 h, the reaction mixture was diluted with ethyl acetate and saturated aqueous sodium bicarbonate. The mixture was extracted with ethyl acetate, washed with saturated brine, dried with sodium sulfate, filtered and concentrated. Purification by reverse phase HPLC (100% water→100% acetonitrile with 0.1% trifluoroacetic acid) gave the title compounds (275 mg). MS 372.1 (M+1).

Provenance & Evidence