2-Trifluoromethylphenol → 3-cyclopentyl-2-[6-oxo-4-(2-trifluoromethyl-phenoxy)-6H-pyridazin-1-yl]-propionic acid

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Reaction Steps

In an analogous manner to the stepwise sequence outlined in intermediate 19, starting from 4,5-dichloro-2-(tetrahydropyran-2-yl)-2H-pyridazin-3-one (Intermediate 20) and 2-trifluoromethyl-phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[6-oxo-4-(2-trifluoromethyl-phenoxy)-6H-pyridazin-1-yl]-propionic acid as a white solid (2.74 g, 95% for the final step); ES+-HRMS m/e calcd for C19H19N2O4F3 [M+H+] 397.1370, found 397.1367. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.03 (br s, 2H), 1.25-1.77 (m, 7H), 1.88-2.05 (m, 1H), 2.09-2.23 (m, 1H), 5.32 (dd, J=10.6, 3.9 Hz, 1H), 5.92 (d, J=2.4 Hz, 1H), 7.52-7.66 (m, 2H), 7.78-7.94 (m, 2H), 8.17 (d, J=2.4 Hz, 1H), 13.06 (br s, 1H).

Provenance & Evidence