Dichloromethane → HCID 71608033, compound

Participants

Reaction Steps

To a solution of tert-butyl 3-((3-(4-(methylsulfonamido)phenyl)-4-oxo-4H-chromen-7-yl)ethynyl)azetidine-1-carboxylate (103 mgs, 0.209 mmol) in dichloromethane (2 mL), trifluoroacetic acid (0.2 mL, 2.08 mmol) was added and stirred at room temperature. After 2 hours the reaction mixture was concentrated and the residue dried under reduced pressure. The crude material was dissolved in dichloromethane (3 mL) and diisopropylethylamine (0.2 mL) and cyclopropanecarbonyl chloride (0.1 mL) were added, and the mixture stirred at room temperature. After 16 hours, the reaction mixture was concentrated under reduced pressure, and the residue dissolved in tetrahydrofuran (2 mL) and 7N ammonia in methanol (4 mL) was added, and the mixture was stirred for 14 hours. The reaction mixture was then concentrated and chromatographed (SiO2, 5% methanol/ethyl acetate) to provide N-(4-(7-((1-(cyclopropanecarbonyl)azetidin-3-yl)ethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide:

Provenance & Evidence