2,3,6-Trimethylphenol → HCID 57919168, 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 2,3,6-trimethyl-phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[6-oxo-4-(2,3,6-trimethyl-phenoxy)-6H-pyridazin-1-yl]-propionic acid as a white solid (11.5 g, 58% for the final step); LC-MS 371 [M+1]+, tR=3.92 min. Purity on HPLC: 98.5% (214 nm), 99.2% (254 nm), tR=9.92 min. 1H NMR (300 MHz, CDCl3): δ 7.94 (d, 1H, J=2.7 Hz), 7.02 (s, 2H), 5.74 (d, 1H, J=2.7 Hz), 5.52 (dd, 1H, J1=10.2 Hz, J2=5.4 Hz), 2.34˜2.32 (m, 1H), 2.20˜2.16 (m, 1H), 2.29 (s, 3H), 2.18 (s, 3H), 2.05 (s, 3H), 1.79˜1.49 (m, 7H), 1.25˜1.14 (m, 2H).

Provenance & Evidence