5-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine → 3-{2-[(5-Dimethylaminomethyl-2-furyl)methylthio]ethylamino}-4-(3-pyridyl)methylamino-1,2,5-thiadiazole 1-oxide

Participants

Reaction Steps

To the methanol solution of 3-methoxy-4-(3-pyridyl)methylamino-1,2,5-thiadiazole 1-oxide produced in Step A was added a solution of 2-[(5-dimethylaminomethyl-2-furyl)methylthio]ethylamine (4.0 g; 18.7 mmoles) in 30 ml of methanol. The reaction mixture was stirred at ambient temperatures for 18 hours and the solvent was removed in vacuo. The residue was placed on 500 g of silica gel (230-400 mesh) and purified by flash chromatography using a gradient elution of acetonitrile-methanol. After combining the appropriate fractions, the title compound was obtained as an amber oil (4.25 g) containing one mole of methanol.

Provenance & Evidence