Dimethylformamide → HCID 68010272, compound

In a dried reaction flask, the crude 2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-pyrazolo[3,4-f]quinoline-7-carboxylic acid (Compound 1) (0.43 g, about 0.967 mmol), DIEA (0.77 mL, 4.45 mmol) and HATU (2.154 g, 5.665 mmol) were added to a mixed solvent of DMF (3.65 mL) and dichloromethane (6.8 mL) Ammonia gas was passed thereto. The mixture was stirred at room temperature for 24 hr. Water and dichloromethane were added. The mixture was extracted with dichloromethane. The combined organic phase was washed with water and saturated salt water, dried over anhydrous sodium sulfate, and concentrated at reduced pressure to produce a crude yellow solid, which was then washed with methanol and ethyl ether respectively to produce a purified product (0.18 g) in 44.3% yield.

1. customIn a dried reaction flask
2. extractionThe mixture was extracted with dichloromethane
3. washThe combined organic phase was washed with water and saturated salt water
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated at reduced pressure
6. customto produce a crude yellow solid, which
7. washwas then washed with methanol and ethyl ether respectively

ORD record

ord-ac200042eae94478944b9a80364798cc

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946279B2