Propionic Acid → HCID 178493983, compound

Participants

Reaction Conditions

Reaction Steps

To a glass microwave vial was added tert-butyl(trans-3-((3-aminopyridin-2-yl)amino)cyclobutyl)carbamate (intermediate 12, step 2, 1.7367 g, 6.24 mmol), tetramethyl orthocarbonate (16.66 ml, 125 mmol), and propionic acid (0.233 ml, 3.12 mmol). The reaction mixture was heated at 100° C. for 5 hours then was allowed to cool to room temperature. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic extract was washed with water, brine, and dried over magnesium sulfate before evaporating to dryness under reduced pressure. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage SNAP HP-silica gel column (50 g), eluting with a gradient of 10% to 100% ethyl acetate in hexane, to provide tert-butyl(trans-3-(2-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)cyclobutyl)carbamate (0.968 g, 3.04 mmol, 48.7% yield).

Provenance & Evidence