Hydrochloric Acid → HCID 71040791, compound

Participants

Reaction Steps

A solution of {(R)-4-[5-((RS)-3-cyano-6,7-dihydro-5H-[1]pyrindin-7-ylamino)-2-fluoro-phenyl]-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-yl}-carbamic acid tert-butyl ester (110 mg, 219 μmol) in hydrochloric acid (4M in dioxane; 1.65 ml, 6.58 mmol) was stirred at room temperature and the progress of reaction was followed on TLC. After completion, the mixture was poured into an aqueous saturated solution of sodium bicarbonate, then extracted with ethyl acetate. The combined organic layers were dried over sodium sulphate and the solvent removed leaving a yellow solid. The crude material was purified by flash chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 0:100 as the eluent. The (RS)-7-[3-((R)-2-amino-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-4-yl)-4-fluoro-phenylamino]-6,7-dihydro-5H-[1]pyrindine-3-carbonitrile (12 mg, 14% yield) was obtained as a mixture of epimers and as a yellow solid. MS (ISP): m/z=402.4 [M+H]+.

Provenance & Evidence