1,2-Ethanediamine, N1,N1,N2-trimethyl- → HCID 86700925, Verbindung

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), N,N,N′-trimethylethylenediamine (0.52 mL, 4.0 mmol), DIEA (0.34 mL, 1.965 mmol) and HATU (0.712 g, 1.873 mmol) were added to a mixed solvent of DMF (4.5 mL) and dichloromethane (4.5 mL). The mixture was stirred at room temperature for 4 days. Water and dichloromethane were added. The mixture was extracted with dichloromethane. The combined organic phase was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated at reduced pressure to obtain a crude yellow solid, which was then purified by silica gel column chromatography (dichloromethane:ethyl acetate:methanol=10:10:1) and concentrated. The resulting concentrate was washed with n-hexane to obtain a purified product (0.176 g) in 38.7% yield.

1. customIn a dried reaction flask
2. extractionThe mixture was extracted with dichloromethane
3. washThe combined organic phase was washed with water and brine
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated at reduced pressure
6. customto obtain a crude yellow solid, which
7. customwas then purified by silica gel column chromatography (dichloromethane:ethyl acetate:methanol=10:10:1)
8. concentrationconcentrated
9. concentrationThe resulting concentrate
10. washwas washed with n-hexane

ORD-Eintrag

ord-0060f943a4434a74bc24b29539c3b8ce

Quelldatensatz

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08946279B2