Trifluoroacetic acid → N-(4-(7-((1-isobutylazetidin-3-yl)ethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide

Participants

Reaction Steps

To a mixture of N-(4-(7-(azetidin-3-ylethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide.trifluoroacetic acid salt (75 mgs, 0.190 mmol) in 1,2-dichloroethane/tetrahydrofuran (3 mL/0.5 mL), was added isobutyraldehyde (0.03 mL, 0.285 mmol), triethylamine (0.05 mL, 0.38 mmol) and sodium triacetoxyborohydride (60 mgs, 0.285 mmol). The mixture was stirred at room temperature for 16 hours, then the reaction mixture was quenched by adding aqueous 1N sodium hydroxide, and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was triturated and washed with diethylether to give N-(4-(7-((1-isobutylazetidin-3-yl)ethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide:

Provenance & Evidence