Dimethylformamide → HCID 136389294, compound

Participants

Reaction Conditions

Reaction Steps

To 1 ml of a DMF solution containing 45 mg of {2-(3-ethoxy-5-hydroxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester (Example (78a)), 11 mg of 2-hydrazinopyrimidine and 0.014 ml of triethylamine were added. The resulting mixture was stirred at 85° C. for one day under a nitrogen atmosphere and then concentrated. The residue was dissolved in 1 ml of methanol, 1 ml of THF, and 0.1 ml of acetic acid, and 100 mg of sodium cyanotrihydroborate was further added thereto. The mixture was stirred at room temperature for 3 hours. The reaction mixture was crudely purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid) to give a crude product of 5-{(3-ethoxy-5-hydroxyphenyl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-2-pyrimidin-2-yl-2,4-dihydro-[1,2,4]triazol-3-one.

Provenance & Evidence