Guaiacol → HCID 57919111, 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 2-methoxy-phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[4-(2-methoxy-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid as a white solid (614.1 mg, 95% for the final step); ES+-HRMS m/e calcd for C19H22N2O5 [M+H+] 359.1602, found 359.1601. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.11 (s, 2H), 1.31-1.78 (m, 7H), 1.86-2.06 (m, 1H), 2.09-2.24 (m, 1H), 3.79 (s, 3H), 5.30 (dd, J=10.7, 4.1 Hz, 1H), 5.59 (d, J=2.7 Hz, 1H), 7.05 (td, J=7.5, 1.5 Hz, 1H), 7.23-7.40 (m, 3H), 8.10 (d, J=2.7 Hz, 1H), 13.02 (br s, 1H).

Provenance & Evidence