Hydrochloric Acid → HCID 178464044, compound

Participants

Reaction Conditions

Reaction Steps

To an ice-cold solution of 29.4 g (59.1 mmol) of [2-[[2-[2-(diethylamino)ethyl]-8-hydroxy-2H-[1]benzothiopyrano[4,3,2-cd]indazol-5-yl]amino]ethyl]-carbamic acid; 1,1-dimethylethyl ester and 800 mL of absolute ethyl alcohol was slowly bubbled anhydrous hydrogen chloride until the temperature reached 12° C. The mixture was cooled to 3° C., and the bubbling process was repeated three times, then the mixture was warmed to 25° C. After stirring overnight, the solids were collected by filtration then stirred for 30 minutes at 5° C. with a solution of 250 mL of water and 800 mL of ethyl alcohol. The mixture was diluted with an additional 250 mL of ethyl alcohol and stirred at 5° C. for 5 hr, then at -5° C. for 30 minutes. The solids were collected by filtration, washed successively with diethyl ether then hexane, and dried over phosphorus pentoxide at 2 mm/40° C./2 hr then at 2 mm/25° C./48 hr to give 27.6 g (90.5%) of 4 as the trihydrochloride salt and solvated with 0.5 equivalents of water, mp 260°-264° C. (dec), 99.4% pure by HPLC.

Provenance & Evidence