Dimethylformamide → N-(1-(2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-pyrazolo[3,4-f]quinoline-7-car bonyl)piperidin-4-yl)methanesulfonamide

Participants

Reaction Steps

In a dried reaction flask, 2-chloro-4-(3-chloro-5-cyclopentyl-4,5-dihydro-1H-pyrazole-1-yl)benzonitrile (420 mg, 1 mmol), N-piperidine-4-ylmethanesulfonamide hydrochloride (280 mg, 1.30 mmol), DIEA (0.52 mL, 3 mmol), and HATU (418 mg, 1.1 mmol) were added to a mixed solvent of CH2Cl2 (10 mL) and DMF (5 mL). The mixture was stirred at room temperature for 3 hr. LC-MS monitored that the starting materials vanished. The solution was evaporated at reduced pressure. Water was added to the residue and the mixture was extracted with ethyl acetate. The combined organic phase was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to produce a yellow powdery solid, which was washed with water and anhydrous ethyl ether to obtain a yellow powdery solid (532 mg) in 91.74% yield.

Provenance & Evidence