2-Methanesulfonylphenol → 3-cyclopentyl-2-[4-(2-methanesulfonyl-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-methanesulfonyl-phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[4-(2-methanesulfonyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (15 g, 68%) as a white solid; LC-MS: [M+H+]=407; HPLC (0.17% trifluoroacetic acid in acetonitrile/water, 50%-100% acetonitrile, gradient, 1 mL/min, Venusil MP-C18, C18-15 cm×4.6 mm-5 μm), purity 98%. 1H-NMR (300 MHz, DMSO-d6) δ 1.42 (m, 2H), 1.55 (m, 7H), 1.57 (s, 1H), 1.59 (s, 1H), 3.31 (s, 1H), 5.31 (m, 1H), 7.63 (m, 1H), 7.87 (s, 2H), 7.98 (m, 1H), 8.19 (s, 1H).

Provenance & Evidence