4-Cyanobenzoic acid → HCID 178457787, compound

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The title compound was prepared using a method analogous to the preparation of (E)-N-(1-(cis-4-(isopropylcarbamoyl)cyclohexyl)-6-(2-(piperidin-1-yl)ethoxy)-1H-imidazo[4,5-c]pyridin-2(3H)-ylidene)benzo[b]thiophene-6-carboxamide, using 4-cyanobenzoic acid. After preparative HPLC purification, the TFA salt was free-based using an SCX-ion exchange column to obtain (E)-4-cyano-N-(1-(cis-4-(isopropylcarbamoyl)cyclohexyl)-6-(2-(piperidin-1-yl)ethoxy)-1H-imidazo[4,5-c]pyridin-2(3H)-ylidene)benzamide as a light yellow solid (34.6% yield). MS m/z=558.2 [M+H], calc 557.69 for C31H39N7O3.

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