5,6,7,8-Tetrahydro-1-naphthol → HCID 57919149, 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 5,6,7,8-tetrahydro-naphthalen-1-ol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[6-oxo-4-(5,6,7,8-tetrahydro-naphthalen-1-yloxy)-6H-pyridazin-1-yl]-propionic acid (13.02 g, 90%) as a white solid; LC-MS 383 [M+H+]; HPLC [acetonitrile (0.1% trifluoroacetic acid) in water (0.1% trifluoroacetic acid)=50%˜100%, gradient, 1 mL/min, Venusil MP-C18, C18-15 cm×4.6 mm-5 μm), 254 nm, 95%, 214 nm, 95%. 1H-NMR (300 MHz, CDCl3): δ 7.88 (s, 1H), 7.15 (t, J=7.8 Hz, 1H), 7.03 (d, J=7.8 Hz, 1H), 6.83 (d, J=7.8 Hz, 1H), 5.88 (s, 1H), 5.50 (q, J=4.8 Hz, 1H), 2.81 (s, 2H), 2.55 (s, 2H), 2.17-2.40 (m, 1H), 2.09-2.16 (m, 1H), 1.50-1.90 (m, 11H), 1.14-1.21 (m, 2H).

Provenance & Evidence