m-Trifluoromethylphenylacetonitrile → HCID 57919155, compound

Participants

Reaction Steps

In an analogous manner to the stepwise sequence outlined in Intermediate 63, starting from 4,5-dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one (Intermediate 20) and (3-trifluoromethyl-phenyl)acetonitrile and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[6-oxo-4-(3-trifluoromethyl-benzyl)-6H-pyridazin-1-yl]-propionic acid (200.1 mg, 70% for Step 5) as a yellow solid; ES+-HRMS m/e calcd for C20H21N2O3F3 [M+H+] 395.1577, found 395.1576. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.99 (br s, 2H), 1.30-1.78 (m, 7H), 1.83-2.05 (m, 1H), 2.07-2.24 (m, 1H), 3.99 (s, 2H), 5.31 (dd, J=10.6, 4.2 Hz, 1H), 6.73 (s, 1H), 7.50-7.69 (m, 3H), 7.73 (s, 1H), 7.95 (d, J=1.8 Hz, 1H), 12.97 (br s, 1H).

Provenance & Evidence