2,6-Difluorophenol → 3-cyclohexyl-2-[4-(2,6-difluoro-phenoxy)-6-oxo-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 2,6-difluoro-phenol and alkylating with 2-bromo-3-cyclohexyl-propionic acid methyl ester (Intermediate 12) afforded 3-cyclohexyl-2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid as a white solid (1.3 g, 99% for the final step); ES+-HRMS m/e calcd for C19H20N2O4F2 [M+H+] 379.1464, found 379.1463. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.63-1.31 (m, 6H) 1.33-2.19 (m, 7H) 5.38 (dd, J=10.9, 3.9 Hz, 1H) 6.08 (br s, 1H) 7.24-7.56 (m, 3H) 8.26 (d, J=2.7 Hz, 1H) 13.11 (br s, 1H).

Provenance & Evidence