Diisopropylethylamine → HCID 11964600, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-amino-5-pyridazin-3-yl-4-trifluoromethyl-benzoic acid methyl ester (79 mg, 0.266 mmol) in dioxane (4 mL) under argon was added 4-chlorophenyl chloroformate (44.6 μL, 0.319 mmol). The solution was stirred at 85° C. for 30 min and cooled to r.t. CH3SO2NHNH2 (58.5 mg, 0.531 mmol) and i-Pr2NEt (46.4 μL, 0.266 mmol) were added and the reaction mixture was heated back to 85° C. for 3 h. The mixture was concentrated in vacuo and the residue was purified by two consecutive flash chromatographies (silica gel, DCM→5% MeOH in DCM) then (silica gel, 7:3 EtOAc/hexanes). The product was suspended in a minimum amount of EtOAc, sonicated then taken into hexanes. The solid was collected by vacuum filtration to furnish the title compound (13 mg, 12%) as a white solid. API-ES: m/z 402.0 [M+H]+, rt 3.36 min, Method N—05—100: 5%→100% (6 min), 100% (1.5 min), 100%→5% (0.5 min)

Provenance & Evidence