N-(1-Cyano-piperidin-4-yl)-N-cyclopropyl-4-oxazol-5-yl-benzamide → N-Cyclopropyl-N-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yl]-4-oxazol-5-yl-benzamide

Participants

Reaction Conditions

Reaction Steps

A 0.5 M solution of zinc chloride in tetrahydrofuran (5.20 mL) is added dropwise at room temperature to a mixture of N-hydroxy-isobutyramidine (266 mg) and N-(1-cyano-piperidin-4-yl)-N-cyclopropyl-4-oxazol-5-yl-benzamide (600 mg) in ethyl acetate (25 mL). The reaction mixture is stirred at 50° C. for 3 h and cooled to room temperature. The precipitate is filtered off and heated to 100° C. for 2 h in a mixture of ethanol (10 mL) and glacial acetic acid (5 mL). The solvents are evaporated and the residue is chromatographed on silica gel [ethyl acetate/cyclohexane/methanol 9:9:2] to give the title compound. LC (method 6): tR=1.66 min; Mass spectrum (ESI+): m/z=422 [M+H]+.

Provenance & Evidence