Dichloromethane → HCID 71136707, compound

Participants

Reaction Steps

To a round bottom flask was added tert-butyl 4-{1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-2,2-dioxido-1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridin-5-yl}-3-hydroxypiperidine-1-carboxylate (27-1) (74 mg, 0.156 mmol), anhydrous DCM (1 mL), the reaction mixture was cooled to 0 C while stirring under an atmosphere of nitrogen, then added DAST (0.035 ml, 0.265 mmol) dropwise. Reaction mixture was continued to stir at 0 C for 10 minutes, then permitted to warm to room temperature. After 1 hour reaction mixture was diluted with MeOH & drops of water, then purified by reverse-phase chromatography (10-100% CH3CN:0.1% TFA in H2O) to yield tert-Butyl 4-{1-[(2,2-difluorocyclopropypmethyl]-3-methyl-2,2-dioxido-1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridin-5-yl}-3-fluoropiperidine-1-carboxylate (29-1). HRMS (M+H)+: observed=477.1785, calculated=477.1778.

Provenance & Evidence