Methanesulfonyl chloride → HCID 86619141, compound

Participants

Reaction Steps

125 mg of the 4-[8-(difluoromethyl)imidazo[1,2-a]pyridin-3-yl]-2-({1-[3-(hydroxymethyl)phenyl]ethyl]amino]pyrimidin-5-carbonitrile [101-1] and 259 μL of N,N-diisopropylethylamine were dissolved in 3 mL of chloroform, then 69 μL of methanesulfonyl chloride was added under an ice-cold condition, and stirred at the same temperature for 30 minutes. Thereto, a saturated aqueous solution of sodium hydrogen carbonate was added, and extracted with chloroform. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The insolubles were filtered and the filtrate was concentrated under reduced pressure to obtain a residue. The residue was dissolved in 3 mL of N,N-dimethylformamide. Thereto, 97 mg of sodium azide was added, and stirred at 80° C. for 1 hour. The reaction solution was cooled back to room temperature, then a saturated aqueous solution of sodium hydrogen carbonate was added, and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The insolubles were filtered and the filtrate was concentrated under reduced pressure to obtain a residue. The residue was purified by preparative thin-layer chromatography, and 87 mg of 2-({1-[3-(azidomethyl)phenyl)ethyl}amino)-4-[8-(difluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-5-carbonitrile [102-1] was obtained as a light brown oily product.

Provenance & Evidence