Ammonia → HCID 178513635, compound

Participants

Reaction Conditions

Reaction Steps

To (R)-methyl 6-(5-(3-(pyrrolidine-1-carbonyl)piperidin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)picolinate (200 mg, 0.460 mmol) in toluene (5 mL) were added sequentially a freshly prepared saturated solution of ammonia in dioxane (10 mL) at −20° C., and trimethylaluminum (0.099 g, 1.348 mmol). The reaction vessel was sealed and was heated at 100° C. for 16 h. The mixture was cooled to room temperature and was partitioned between ethyl acetate, and water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was triturated twice with methanol:diethyl ether (1:10) to afford the title compound (40 mg). MS (ES+) (M+H) 420.2892; LCMS retention time 3.71 min (Method I1).

Provenance & Evidence