Cyclopropanecarboxylic acid → HCID 68378922, compound

Participants

Reaction Conditions

Reaction Steps

An 8-mL vial was charged with cyclopropanecarboxylic acid (78.5 μL, 0.99 mmol) and DMF (1.0 mL). Carbonyldiimidazole (176 mg, 1.09 mmol) was added to the vial at room temperature. The clear reaction mixture was stirred for 2 h and then added to another 8-mL vial containing {1-[5-(N-hydroxycarbamimidoyl)-pyridin-2-yl]-cyclopropyl}-carbamic acid tert-butyl ester (430 mg, 1.47 mmol) in 1.0 mL of DMF. The resulting pale yellow reaction mixture was stirred at room temperature for 30 min and then heated at 100° C. for 16 h. The clear pale orange reaction mixture was quenched with water (10 mL) and extracted with ethyl acetate (2×20 mL). The organics were washed with of water (2×15 mL) and brine (15 mL), dried over Na2SO4, filtered, and concentrated to a crude oil. The crude oil was purified via normal phase flash chromatography on silica gel, eluting with 0-35% EtOAc/hexanes, to give {1-[5-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)-pyridin-2-yl]-cyclopropyl}-carbamic acid tert-butyl ester (86 mg, 26%) as a white solid.

Provenance & Evidence