Dimethylformamide → 2-(3-{(8-methoxy-4H-benzo[1,3]dioxin-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-5-oxo-4,5-dihydro[1,2,4]triazol-1-yl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

To 2 ml of a DMF solution containing 130 mg of [2-(8-methoxy-4H-benzo[1,3]dioxin-6-yl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene]carbamic acid methyl ester (Example (21h)), 46 mg of 2-hydrazinobenzoic acid hydrochloride and 0.200 ml of triethylamine were added. The resulting mixture was stirred at 80° C. for 8 hours under a nitrogen atmosphere, and then the reaction mixture was concentrated. The residue was dissolved in 3 ml of methanol and 0.3 ml of acetic acid, and 250 mg of sodium cyanotrihydroborate was added thereto. The mixture was stirred at room temperature overnight. To this reaction mixture, water was added and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by NAM silica gel column chromatography (methanol-ethyl acetate) to give 2-(3-{(8-methoxy-4H-benzo[1,3]dioxin-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-5-oxo-4,5-dihydro[1,2,4]triazol-1-yl)benzoic acid.

Provenance & Evidence