Methyl iodide → HCID 71140764, compound

Participants

Reaction Steps

To a 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) (54 mg, 0.114 mmol), & anhydrous THF (2.5 mL). The reaction mixture was cooled to 0 C while stirring under an atmosphere of nitrogen, then added sodium hydride (60% by wt in mineral oil) (5.92 mg, 0.148 mmol) in one portion. Reaction mixture was continued to stir at 0 C for 10 minutes, then added iodomethane (8.54 μl, 0.137 mmol) and 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-difluorocyclopropyl)methyl]-3-methyl-2,2-dioxido-1,3-dihydro[1,2,5]thiadiazole-[3,4-b]pyridin-5-yl}-3-methoxypiperidine-1-carboxylate (28-1). HRMS (M+H)+: observed=489.1983, calculated=489.1978.

Provenance & Evidence