Hydrochloric Acid → HCID 178434426, compound

Participants

Reaction Steps

A solution of 1.8 g (2.55 mmol) of 5-(4-(benzyloxy)-3-(trifluoromethyl)phenyl)-3-(4-methoxybenzyl)-1-methyl-9-(piperazin-1-yl)-3H-benzo[f]pyrazolo[3,4-c][2,7]naphthyridin-6(7H)-one dissolved in 25 ml of trifluoroacetic acid is carried at 70° C. for 3 hours. After returning to room temperature, 50 ml of diisopropyl ether is added until a stable precipitate appears; the latter is filtered and then taken up in water. Acidity is neutralized by the addition of 1 M soda. The solid is filtered again and then triturated several times in hot methanol to yield after a final filtration 950 mg of 5-(4-hydroxy-3-(trifluoromethyl)phenyl)-1-methyl-9-(piperazin-1-yl)-3H-benzo[f]pyrazolo[3,4-c][2,7]naphthyridin-6(7H)-one. The product is then taken up in 20 ml of anhydrous dioxane; a 4 M solution of hydrochloric acid in dioxane (932 μl, 3.73 mmol) is added and the reaction medium is stirred at room temperature for 2 hours. The precipitate is filtered, rinsed with dioxane and triturated in methanol to yield 475 mg (36%) of 5-(4-hydroxy-3-(trifluoromethyl)phenyl)-1-methyl-9-(piperazin-1-yl)-3H-benzo[f]pyrazolo[3,4-c][2,7]naphthyridin-6(7H)-one hydrochloride in the form of a yellow solid.

Provenance & Evidence