2-Cyclopentylphenol → HCID 57919158, 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-cyclopentyl-phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[4-(2-cyclopentyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (12.89 g, 88%) as a white solid; LC-MS [M+H+]=397; HPLC (0.1% trifluoroacetic acid in acetonitrile/water, 50%-100% acetonitrile, gradient, 1 mL/min, Venusil MP-C18, C18-150 cm×4.6 mm-5 μm), 214 nm, 97.39%, 254 nm, 96.72%. 1H-NMR (300 MHz, CDCl3) δ 7.88 (s, 1H), 7.29-7.41 (m, 1H), 7.22-7.26 (m, 2H), 6.98-7.01 (m, 1H), 5.91-5.92 (d, J=3, 1H), 5.49-5.54 (m, 1H), 3.03-3.12 (m, 1H), 2.28-2.38 (m, 1H), 2.09-2.18 (m, 1H), 1.95-1.98 (d, J=9 Hz, 2H), 1.50-1.79 (m, 13H), 1.09-1.26 (m, 2H).

Provenance & Evidence