Acetic Acid → HCID 24803423, compound

Participants

Reaction Steps

Stir a solution of 2-(4-chloro-phenyl)-6-[3-methoxy-4-((R)-piperidin-3-yloxy)-phenyl]-6H-thieno[2,3-c]pyridine-7-one (446 mg, 0.96 mmol), formaldehyde (0.38 mL, 37% aqueous solution), and acetic acid (0.22 mL, 3.84 mmol) in methanol (34 mL) at room temperature for 5 min. Add sodium cyanoborohydride (150 mg, 2.4 mmol) to this solution and stir the reaction for 2 h. Concentrate the mixture in vacuo and partition the residue between dichloromethane (20 mL) and saturated sodium bicarbonate (20 mL). Separate the organic portion and extract the aqueous portion with dichloromethane (2×10 mL). Dry the combined organics (Na2SO4), filter, and concentrate in vacuo. Purify by chromatography (dichloromethane to 5% 2 M ammonia in methanol/dichloromethane) to afford 158 mg (34%) of 2-(4-chloro-phenyl)-6-[3-methoxy-4-((R)-1-methyl-piperidin-3-yloxy)-phenyl]-6H-thieno[2,3-c]pyridin-7-one.

Provenance & Evidence