Cyanogen Bromide → HCID 86626303, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl 4-[(3-amino-2-chloroquinolin-4-yl)amino]butylcarbamate (Nanba et al, U.S. Pat. No. 6,069,149, Example 14, 9.5 g, 26 mmol) in ethanol (100 mL) was heated to 110° C.; cyanogen bromide (2.98 g, 28.6 mmol) was added. The reaction was stirred for three hours at 110° C., and an analysis by LC/MS indicated the presence of starting material. Additional cyanogen bromide (0.55 equivalent) was added, and the reaction was stirred for three days at 110° C. and allowed to cool to room temperature. Most of the solvent was removed under reduced pressure, and 2 N aqueous sodium hydroxide (500 mL) was added. The mixture was stirred for 30 minutes, and ethyl acetate (400 mL) was added. A precipitate formed and was isolated by filtration to provide 7.188 g of tert-butyl 4-(2-amino-4-chloro-1H-imidazo[4,5-c]quinolin-1-yl)butylcarbamate as a cream-colored solid.

Provenance & Evidence