Dimethyl Sulfoxide → Tert-butyl cis-2-(5-aminocarbonyl-3-fluoro-6-(5-methylpyridin-3-ylamino)pyridin-2-ylamino)cyclohexylcarbamate

Participants

Reaction Conditions

Reaction Steps

A 5N sodium hydroxide aqueous solution (1.18 ml) and 30% hydrogen peroxide solution (0.70 ml) were added to a solution of dimethyl sulfoxide (10 ml) and ethanol (10 ml) containing tert-butyl cis-2-(6-(5-methylpyridin-3-ylamino)-5-cyano-3-fluoropyridin-2-ylamino)cyclohexylcarbamate (520 mg), followed by stirring at 34° C. for 30 minutes. The reaction mixture was cooled to room temperature, and water was added. Solid matter was collected by filtration, dissolved in ethyl acetate and tetrahydrofuran, washed with water and then with saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure. The obtained residue was added to diisopropylether, solid matter was collected by filtration and washed with diisopropylether and hexane, and a light yellow solid of tert-butyl cis-2-(5-aminocarbonyl-3-fluoro-6-(5-methylpyridin-3-ylamino)pyridin-2-ylamino)cyclohexylcarbamate (506 mg) was thus obtained.

Provenance & Evidence