3-Cyanobenzoic acid → 4-cyano-N-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide

Participants

Reaction Conditions

Reaction Steps

To 5-amino-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (step b) (30 mg, 0.138 mmol) in 1.0 mL acetonitrile was added HATU (104 mg, 0.273 mmol), 3-cyano benzoic acid (30 mg, 0.203 mmol) and DIPEA (48.0 ul). The reaction mixture was heated to 80° C. for five hours. Cooled the reaction mixture and light yellow precipitate was filtered, washed with acetonitrile to yield 4-cyano-N-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide. The crude product was further dissolved in 1.0 mL ethanol, added hydantoin (10 mg, 0.01 mmol) and pipperdine (9.5 ul). The reaction was heated to 80° C. for three hours. Cooled the reaction mixture and precipitate was filtered, washed with ethanol to yield 7 mg (40% yield, two steps) (Z)-4-cyano-N-(7-(cyclopropylamino)-3-((2,5-dioxoimidazolidin-4-ylidene)methyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide. LCMS (M+1=429)

Provenance & Evidence