Dimethylformamide → HCID 178437607, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-[4-({4-[({4-[(E)-2-(2-ethyl-1,3-thiazol-4-yl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy}methyl)-5-methyl-1,3-oxazol-2-yl]benzonitrile (350 mg), sodium azide (55 mg), ammonium chloride (59 mg) and N,N-dimethylformamide (10 mL) was stirred at 120° C. for 6 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate-tetrahydrofuran. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:5-1:2-1:1, v/v) to give 5-{3-[4-({4-[({4-[(E)-2-(2-ethyl-1,3-thiazol-4-yl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy}methyl)-5-methyl-1,3-oxazol-2-yl]phenyl}-1H-tetrazole (106 mg, yield 28%) as colorless crystals. Recrystallization from ethyl acetate-diethyl ether gave colorless prism crystals. melting point: 144-147° C.

Provenance & Evidence