Acetic Acid → HCID 57911418, compound

Participants

Reaction Steps

SODIUM CYANOBOROHYDRIDE (108 mg, 1.721 mmol) was added to the Acetonitrile (2 mL) solution of (6R,9R)-2-amino-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate (46 mg, 0.086 mmol) and FORMALDEHYDE (1 mL, 13.43 mmol) at rt. The reaction was stirred at room temperature for 4 hours. ACETIC ACID (0.5 mL, 8.73 mmol) was added to the reaction mixture and the reaction was stirred overnight. Volatile was removed mostly via vacuum and the crude was added NaOH (1N) and stirred at room temperature for 1 hour before extract with ethyl acetate. The ethyl acetate layer was dried (Na2SO4), filtered and concentrated. Flash column by methanol in CH2Cl2 from 0 to 4% to 8% gave the desired product (19.8 mg, 39%). MS (ESI)[M+H+]=563.42.

Provenance & Evidence