4,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one → HCID 57919178, 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-hydroxy-quinoline and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[6-oxo-4-(quinolin-5-yloxy)-6H-pyridazin-1-yl]-propionic acid (20 g, 83%) as a solid; LC-MS, [M+H+]=380.2; HPLC (0.17% trifluoroacetic acid in acetonitrile/water, 30%-90% acetonitrile, gradient, 1 mL/min, Venusil MP-C18, C18-15 cm×4.6 mm-5 μm) 254 nm, 95.8%; 214 nm, 99.8%. 1H-NMR (300 MHz, CDCl3): δ 1.12-1.25 (m, 2H), 1.50-1.84 (m, 7H), 2.11-2.20 (m, 1H), 2.33-2.43 (m, 1H), 5.54-5.59 (dd, J=10.5, 4.5 Hz, 1H), 5.94-5.95 (d, J=2.7 Hz, 1H), 7.34-7.37 (d, J=7.8 Hz, 1H), 7.48-7.53 (dd, J=8.7, 4.5 Hz, 1H), 7.74-7.80 (t, 1H), 8.00-8.01 (d, J=3.0 Hz, 1H), 8.14-8.16 (d, J=8.4 Hz, 1H), 8.28-8.31 (d, J=8.4 Hz, 1H), 9.02-9.03 (d, J=3.0 Hz, 1H).

Provenance & Evidence