3-(Trifluoromethyl)phenol → HCID 57919281, compound

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 3-trifluoromethyl-phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[6-oxo-4-(3-trifluoromethyl-phenoxy)-6H-pyridazin-1-yl]-propionic acid as a white solid (774.7 mg, 93% for the final step); ES+-HRMS m/e calcd for C19H19N2O4F3 [M+H+] 397.1370, found 397.1368. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.99-1.21 (m, 2H), 1.35-1.77 (m, 7H), 1.97 (ddd, J=13.7, 9.1, 4.3 Hz, 1H), 2.15-2.26 (m, 1H), 5.33 (dd, J=10.9, 4.3 Hz, 1H), 5.87 (d, J=2.8 Hz, 1H), 7.66 (d, J=7.0 Hz, 1H), 7.71-7.81 (m, 3H), 8.14 (d, J=2.8 Hz, 1H), 13.03 (br s, 1H).

Provenance & Evidence