Reacción #1932042

Ecuación de reacción

2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-pyrazolo[3,4-f]quinoline-7-carboxylic acid

thiomorpholine-1,1-dioxide hydrochloride

DIEA

HATU

→

product

Rendimiento 76.2%

2-chloro-4-(3-cyclopentyl-7-(1,1-dioxidothiomorpholine-4-carbonyl)-3,3a,4,5-tetrahydro-2h-pyrazolo[3,4-f]quinolin-2-yl)benzonitrile

Rendimiento 76.2%

Disolventes

dichloromethane

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónwas concentrated under reduced pressure
2. 2
   workup.ADDITIONWater was added to the residue
3. 3
   FiltraciónThe mixture was filtered
4. 4
   Otroto produce a crude yellow solid, which
5. 5
   Lavadowas washed with methanol

Procedimiento

In a dried reaction flask, 2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-pyrazolo[3,4-f]quinoline-7-carboxylic acid (0.421 g, 1.0 mmol), thiomorpholine-1,1-dioxide hydrochloride (0.223 g, 1.3 mmol), DIEA (0.26 mL, 1.49 mmol), and HATU (0.418 g, 1.1 mmol) were added to a mixed solvent of DMF (4 mL) and dichloromethane (8 mL). The mixture was stirred at room temperature for 1.5 hr and was concentrated under reduced pressure. Water was added to the residue. The mixture was filtered to produce a crude yellow solid, which was washed with methanol to obtain a purified product (0.410 g) in 76.2% yield.

Fuente