Triethylamine → N-{(6S,9R)-6-(2,3-Difluorophenyl)-3-[1-(trifluoromethyl)cyclopropyl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-9-yl}-1-oxo-2,8-diazaspiro[4,5]decane-8-carboxamide

Participants

Reaction Conditions

Reaction Steps

Triethylamine (16 μL, 0.112 mmol) was added to a solution of the bis hydrochloride salt of (6S,9R)-6-(2,3-difluorophenyl)-3-[1-(trifluoromethyl)cyclopropyl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-9-amine (20 mg, 0.045 mmol) and 1,1′-carbonyldiimidazole (13 mg, 0.079 mmol) in tetrahydrofuran (1.0 mL) at 0° C. After 20 min, additional 1,1′-carbonyldiimidazole (7.3 mg, 0.045 mmol) was added. After 30 min, the hydrochloride salt of 2,8-diazaspiro[4.5]decan-1-one (11 mg, 0.056 mmol) and dichloromethane (1.0 mL) were added and the mixture was heated to 60° C. After 16 h, the reaction was concentrated. Purification by reverse phase HPLC (C-18, 10% acetonitrile/water→100% acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (14 mg). MS 553.2315 (M+1).

Provenance & Evidence