(1,1'-Biphenyl)-2-ol → 2-[4-(biphenyl-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentylpropionic 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 biphenyl-2-ol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 2-[4-(biphenyl-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentylpropionic acid (15.4 g, 75%) as a solid; 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>96% (214 nm). 1H-NMR (CDCl3, 300 MHz) δ0.97-1.10 (m, 2H), 1.45-1.69 (m, 7H), 2.00-2.07 (m, 1H), 2.17-2.22 (m, 1H), 5.39 (dd, J=10.5, 1H), 5.83 (s, 1H), 7.17 (d, J=7.5, 1H), 7.24-7.48 (m, 8H), 7.65 (s, 1H).

Provenance & Evidence