Water → HCID 178509707, compound

Participants

Reaction Steps

To a solution of (R)-(1-(6-amino-5-nitropyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (Intermediate 1, Step 3) (50 mg, 0.15 mmol) and 3-formylbenzonitrile (34 mg, 0.31 mmol) in ethanol (2 mL) were added sodium dithionite (52 mg, 0.4 mmol), and water (0.5 mL). After 20 h at 80° C., the mixture was concentrated. The residue was partitioned between water and ethyl acetate. The organic layer was concentrated under reduced pressure and the resulting residue was purified by preparative TLC to afford (R)-3-(5-(3-(pyrrolidine-1-carbonyl)piperidin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)benzonitrile as a yellow solid (40 mg, 81%). MS (ES+APCI) (M+H) 401.0; HPLC retention time 4.016 min (Method I).

Provenance & Evidence