1-Naphthol → HCID 57919189, 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 naphthalen-1-ol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[4-(naphthalen-1-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (9.1 g, 80%) as a solid; ESI-MS 379 [M+H+]; 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), >96% (purity). 1H-NMR (300 MHz, CDCl3) δ 8.22-8.21 (d, 1H), 8.05-7.91 (m, 3H), 7.65-7.58 (m, 3H), 7.42-7.39 (d, 1H), 5.78-5.77 (t, 1H), 5.53-5.48 (m, 1H), 2.45-2.35 (m, 1H), 2.17-2.04 (m, 1H), 1.85-1.14 (m, 9H).

Provenance & Evidence