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

Participants

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 4-trifluoromethyl-phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[6-oxo-4-(4-trifluoromethyl-phenoxy)-6H-pyridazin-1-yl]-propionic acid as a white solid (715.2 mg, 88% for the final step); ES+-HRMS m/e calcd for C19H19N2O4F3 [M+H+] 397.1370, found 397.1371. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.99-1.20 (m, 2H), 1.34-1.79 (m, 7H), 1.91-2.05 (m, 1H), 2.12-2.26 (m, 1H), 5.33 (dd, J=10.8, 4.2 Hz, 1H), 6.01 (d, J=2.9 Hz, 1H), 7.54 (d, J=8.5 Hz, 2H), 7.90 (d, J=8.5 Hz, 2H), 8.14 (d, J=2.9 Hz, 1H), 13.03 (br s, 1H).

Provenance & Evidence