3-(Trifluoromethoxy)benzoic acid → HCID 178457789, compound

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Reaction Steps

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 3-(trifluoromethoxy)benzoic acid. The material was purified via preparative HPLC (0.1% NH4OH in ACN/H2O) to provide (E)-N-(1-(cis-4-(isopropylcarbamoyl)cyclohexyl)-6-(2-(piperidin-1-yl)ethoxy)-1H-imidazo[4,5-c]pyridin-2(3H)-ylidene)-3-(trifluoromethoxy)benzamide (50.3% yield). MS m/z=617.4 [M+H], calc 616.67 for C31H39F3N6O4. 1H NMR (CDCl3) δ ppm: 12.32 (br. s., 1H), 8.30-8.43 (m, 2H), 8.10 (d, J=0.8 Hz, 1H), 7.28-7.31 (m, 1H), 7.01 (s, 1H), 5.34 (d, J=1.0 Hz, 1H), 4.77-4.91 (m, 1H), 4.45-4.55 (m, 2H), 4.14-4.29 (m, 1H), 2.46-2.95 (m, 8H), 2.20-2.27 (m, 2H), 1.73-1.89 (m, 4H), 1.58-1.73 (m, 5H), 1.41-1.57 (m, 3H), 1.22 (d, J=6.6 Hz, 6H).

Provenance & Evidence