4,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one → HCID 57919263, compound

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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 6-methyl-pyridin-2-ol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[4-(6-methyl-pyridin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (9.7 g, 66% for the final step); LC-MS: tR=3.28 min, 344 [M+H]+. HPLC: tR=9.16 min, 95.62% at 214 nm, 96.87% at 254 nm. 1H NMR (300 MHz, DMSO-d6): δ13.04 (broad, 1H), 8.07 (d, 1H, J=2.4 Hz), 7.89 (t, 1H, J=7.5 Hz), 7.21 (d, 1H, J=7.2 Hz), 7.06 (d, 1H, J=8.4 Hz), 6.52 (d, 1H, J=2.4 Hz), 5.36 (dd, 1H, J=10.5 Hz, J=4.2 Hz), 2.43 (s, 3H), 2.23-2.17 (m, 1H), 2.02-2.00 (m, 1H), 1.70-1.44 (m, 7H), 1.13-1.05 (m, 2H).

Provenance & Evidence