Benzoyl chloride → N-[2-hydroxy-4-[[[(Z)-(6-iodo-1,3-dioxoisoquinolin-4-ylidene)methyl]amino]methyl]phenyl]benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of (4Z)-4-[({4-amino-3-[(triisopropylsilyl)oxy]benzyl}amino)methylene]-6-iodoisoquinoline-1,3(2H,4H)-dione (65 mg, 0.11 mmol) in tetrahydrofuran (6 mL) is added 4-methylmorpholine (36 μL, 0.33 mmol), and the mixture is cooled to 0° C. in an ice-water bath. Benzoyl chloride (38 μL, 0.33 mmol) is added and the mixture is allowed to stir at room temperature for one hour. To the mixture is then added 1.0 M tetrabutylammonium fluoride solution in tetrahydrofuran (1 mL, 1 mmol). After heating for 10 minutes at 55° C., water is added. The precipitated solid is collected by filtration, washed with water and acetonitrile, and dried under house vacuum to give N-[2-hydroxy-4-({[(Z)-(6-iodo-1,3-dioxo-2,3-dihydroisoquinolin-4(1H)-ylidene)methyl]amino}methyl)phenyl]benzamide (34 mg, 58%).

Provenance & Evidence