Piperidin-4-ol → HCID 56849226, 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) (0.4 g, about 0.9 mmol), DIEA (0.5 mL, 2.89 mmol) and HATU (1.047 g, 2.754 mmol) were added to DMF (4.5 mL). To the mixture was added dropwise a solution of dichloromethane (9 mL) dissolved in 4-hydroxylpiperidine (0.446 g, 4.409 mmol) under an ice-salt bath. After the completion of the dropwise addition, the mixture was stirred at room temperature for 4 days. Water and ethyl acetate were added. The mixture was extracted with ethyl acetate. 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 were washed with ethyl ether and ethyl acetate respectively to produce a purified product (0.217 g) in 47.8% yield.

1. customIn a dried reaction flask
2. additionAfter the completion of the dropwise addition
3. extractionThe mixture was extracted with ethyl acetate
4. washThe combined organic phase was washed with water and saturated salt water
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated at reduced pressure
7. customto produce a crude yellow solid, which
8. washwere washed with ethyl ether and ethyl acetate respectively

ORD record

ord-8ef81be73a794fa18ab7c230f50e8e79

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946279B2