Triethylamine → HCID 178455006, compound

Participants

Reaction Steps

To a solution of 6-(1-((tert-butyldimethylsilyl)oxy)cyclopropyl)picolinonitrile (45.0 mg, 0.164 mmol) in ethanol (0.3 mL) was added dropwise a solution of sodium ethoxide in ethanol (0.1 mL, 21 wt %, 0.2 mmol). The reaction mixture was stirred at room temperature for 50 min and then heated to 35° C. for 1.5 h. To the mixture was added (R)-(1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochloride (77.2 mg, 0.2 mmol), triethylamine (47 μL, 0.3 mmol) and acetic acid (47 μL). The reaction mixture was heated to 110° C. for 50 min. The solution was transferred to a microwave vial and it was heated to 145° C. for 20 min. The solvent was removed under reduced pressure to afford (R)-(1-(2-(6-(1-((tert-butyldimethylsilyl)oxy)cyclopropyl)pyridin-2-yl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone. The material was used without further purification.

Provenance & Evidence