Cyclopentanecarboxylic acid → HCID 25230807, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-[3,5-dichloro-4-(1-chloromethyl-5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carbonitrile (0.64 mmol) in acetonitrile (18 mL) at 25° C. was treated with cyclopentanecarboxylic acid (73.4 μL, 0.67 mmol) followed by silver (I) oxide (155.4 mg, 0.67 mmol). The reaction mixture was stirred at 25° C. in the dark for 3 d. At this time, the reaction was filtered through a pad of celite® and was rinsed with a solution of 90/10 methylene chloride/methanol (1×100 mL). The filtrate was then concentrated in vacuo. Biotage flash chromatography (40S, 0.5-1.25% methanol/methylene chloride) followed by reverse phase chromatography (Pursuit C-18 column, acetonitrile gradient with trifluoroacetic acid) followed by lyophilization afforded cyclopentanecarboxylic acid 3-[2,6-dichloro-4-(6-cyano-3,5-dioxo-4,5-dihydro-3H-[1,2,4]triazin-2-yl)-phenoxy]-5-isopropyl-6-oxo-6H-pyridazin-1-ylmethyl ester (75.7 mg, 21%) as an off-white solid. ES+-HRMS m/e calcd for C24H22N6O6Cl2 (M+Na+) 583.0870, found 583.0871.

Provenance & Evidence