Methyl iodide → HCID 22031538, compound

Participants

Reaction Steps

A mixture of 283 mg 6-[3-(4-fluorophenyl)-1-trityl-1H-pyrazol-4-yl]imidazo[1,2-a]pyridine-3-carboxylic acid hydrazide (compound in Production Example 274), 38 mg carbon disulfide, 20 mg sodium hydroxide, 5 mL ethanol and 5 mL water was heated for 4 hours under reflux. Ethyl acetate, tetrahydrofuran and an aqueous saturated ammonium chloride solution were added to the reaction solution, and the organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was evaporated. 285 mg crude product of 5-{6-[3-(4-fluorophenyl)-1-trityl-1H-pyrazol-4-yl]imidazo[1,2-a]pyridin-3-yl}[1,3,4]oxadiazol-2-thiol was obtained as pale yellow crystals. To a mixture of this thiol derivative, 128 mg potassium carbonate and 10 mL N,N-dimethylformamide under ice-coolingd water in a stream of nitrogen was added 32 μL methyl iodide, and the mixture was stirred for 10 minutes. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated, washed twice with water and then with brine and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was evaporated. The resulting residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 148 mg of the title compound as a colorless amorphous.

Provenance & Evidence