2-benzoyl-N-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenyl)hydrazinecarbothioamide → 1,7-dimethyl-3-(2-methyl-5-(5-phenyl-1,3,4-thiadiazol-2-ylamino)phenyl)-1,6-naphthyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

The mixture of crude 2-benzoyl-N-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenyl)hydrazinecarbothioamide 35 and methanesulfonic acid (2 drops) in toluene (1 mL) was heated at 130° C. overnight in a sealed vial. The reaction was evaporated to dryness and the crude residue was purified by preparative LC/MS to give 1,7-dimethyl-3-(2-methyl-5-(5-phenyl-1,3,4-thiadiazol-2-ylamino)phenyl)-1,6-naphthyridin-2(1H)-one (H1). MS m/z 440.1 (M+1).

Provenance & Evidence