Water → HCID 57964981, compound

Participants

Reaction Conditions

Reaction Steps

A solution of cyclohexyl chloroformate (Waterstone Technology, LLC, Carmel, Ind., USA; 42 mg, 0.26 mmol) in dichloromethane (150 μL) was added to a cooled (˜0° C.) solution of 4-(2-methyl-pyridin-3-yloxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine (Intermediate 28; 52 mg, 0.17 mmol), diisopropylethylamine (77 μL, 0.80 mmol) and 4-dimethylaminopyridine (1 mg) in anhydrous dichloromethane (2 mL) over 30 sec. The mixture was stirred at 0° C. for 5 min, then warmed to room temperature and stirred for 1 h. Water (5 mL) was added. The layers were separated and the organic layer was washed with brine, dried (sodium sulfate), filtered, evaporated, and purified on an Isco 4 g column eluting with 0-4% methanol/dichloromethane. Fractions containing the product were pooled, concentrated and lyophilized to give 4-[4-(2-methyl-pyridin-3-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid cyclohexyl ester (9.6 mg, 13%). Mass spectrum (ES) MH+=437.

Provenance & Evidence