Triethylamine → HCID 86730359, compound

Participants

Reaction Steps

Thionyl chloride (118 μL, 1.62 mmol) was added to a solution of benzotriazole (193 mg, 1.62 mmol) in dichloromethane (5 mL) under nitrogen atmosphere at room temperature, and the mixture was stirred for 5 minutes. 4-(1-(tert-Butoxycarbonyl)azetidin-3-yl)benzoic acid described in Production Example 26-5 (300 mg, 1.08 mmol) was added to the reaction liquid, and the mixture was further stirred for 1 hour. The reaction liquid was filtered through anhydrous sodium sulfate on the glass filter, and the resultant was washed with dichloromethane. A solution of triethylamine (748 μL, 5.40 mmol), 4-dimethylaminopyridine (6.60 mg, 0.054 mmol), and 5-((2-aminopyridin-4-yl)oxy)-6-(3-methoxypropoxy)-N-methyl-1H-indole-1-carboxamide described in Production Example 32-8 (200 mg, 0.54 mmol) in tetrahydrofuran (10 mL) was added to the resultant dichloromethane solution under nitrogen atmosphere at 0° C., and the mixture was stirred for 4 hours and 20 minutes. The reaction liquid was diluted with ethyl acetate and water. The organic layer was washed with a saturated saline solution and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration and then the filtrate was concentrated under vacuum. Tetrahydrofuran and an excessive quantity of methylamine tetrahydrofuran solution were added to the residue, and the mixture was stirred at room temperature. The liquid mixture was concentrated under vacuum. The residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=2:3-0:1) to obtain the title compound (146 mg, 43%).

Provenance & Evidence