N-(2-Hydroxybenzoyl)pyrrolidine → HCID 57919304, 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-(pyrrolidine-1-carbonyl)-phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-{6-oxo-4-[2-(pyrrolidine-1-carbonyl)-phenoxy]-6H-pyridazin-1-yl}-propionic acid as a white solid (100 mg, 32% for the final step). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.91-1.18 (m, 2H), 1.31-1.86 (m, 11H), 1.86-2.05 (m, 1H), 2.06-2.21 (m, 1H), 3.10-3.48 (m, 4H), 5.26 (dd, J=10.7, 4.1 Hz, 1H), 5.77 (d, J=2.4 Hz, 1H), 7.36 (d, J=7.8 Hz, 1H), 7.41 (d, J=7.2 Hz, 1H), 7.47-7.60 (m, 2H), 8.00 (d, J=2.4 Hz, 1H), 13.06 (br s, 1H).

Provenance & Evidence