Sodium Methoxide → HCID 178451954, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 3-((2-amino-6-((R)-3-(pyrrolidine-1-carbonyl)piperidin-1-yl)pyridin-3-yl)carbamoyl)piperidine-1-carboxylate in methanol/sec-butanol (1:2, 15 mL) was added a solution of 25% sodium methoxide in methanol (9.0 mL). The reaction mixture was stirred at 90° C. for 16 h. The solvent was removed under reduced pressure and a solution of methanol/dichloromethane (1:9, 50 mL) and a saturated aqueous solution of sodium bicarbonate (50 mL) were added to the residue, and the layers were separated. The aqueous layer was extracted again with methanol/dichloromethane (1:9, 25 mL). The combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified via column chromatography to afford (R)-tert-butyl 3-(5-(3-(pyrrolidine-1-carbonyl)piperidin-1-yl)-3H-imidazo[4,5-b]pyridine-2-yl)piperidine-1-carboxylate.

Provenance & Evidence