1,1'-Thiocarbonyldiimidazole → HCID 86633746, compound

Participants

Reaction Steps

A solution of tert-butyl 3-[(3-amino-7-bromoquinolin-4-yl)amino]propylcarbamate (9.3 g, 23.5 mmol) and 1,1′-thiocarbonyldiimidazole (4.6 g, 26 mmol) in THF (250 mL), and the reaction mixture was heated at reflux for two hours. An analysis by liquid chromatography/mass spectrometry (LC/MS) indicated the reaction was incomplete, and additional 1,1′-thiocarbonyldiimidazole (1 g) was added. The reaction was heated at reflux for an additional hour, allowed to cool to room temperature, and concentrated under reduced pressure. The residue was dissolved in water, and the resulting solution was extracted with tert-butyl methyl ether. The combined organic fractions were washed with water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with a gradient of 2% ammonium hydroxide/methanol in dichloromethane) to provide 4 g of tert-butyl 3-(7-bromo-2-thioxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)propylcarbamate.

Provenance & Evidence