Formic Acid → HCID 178464204, compound

Participants

Reaction Steps

Into a vial containing (R)-(1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochloride (125 mg, 0.3 mmol) was added formic acid (73.5 μL, 1.7 mmol) followed by 2,2,-trifluoroethanol (1.7 mL) and methyl 2,2,2-trichloroacetimidate (47.0 μL, 0.4 mmol). The vial was sealed and stirred at room temperature for 13 min. The reaction mixture was heated to 60° C. and stirred for 3 h at that temperature. An aliquot of 0.3 mL was transferred into another vial containing diethylamine (89.1 μL, 0.9 mmol). The resulting mixture was heated to 60° C. and stirred for 16 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was partitioned between water and ethyl acetate. The aqueous was further extracted with ethyl acetate. The combined organics were concentrated under reduced pressure. The residue was purified via HPLC to afford the title compound. MS (ESI+) (M+H) 399.1; HPLC retention time 1.9864 min (Method A).

Provenance & Evidence