Diisopropylethylamine → 3-oxo-3-[6-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,6-diazaspiro[3.5]non-1-yl]-propionitrile
Reaktionsgleichung
[NH:1]1[C:4]2([CH2:9][CH2:8][CH2:7][N:6]([C:10]3[C:11]4[CH:18]=[CH:17][NH:16][C:12]=4[N:13]=[CH:14][N:15]=3)[CH2:5]2)[CH2:3][CH2:2]1.CC1N([C:25]([CH2:27][C:28]#[N:29])=[O:26])N=C(C)C=1.C(N(CC)C(C)C)(C)C.C(=O)(O)[O-].[Na+]>O1CCOCC1>[O:26]=[C:25]([N:1]1[C:4]2([CH2:9][CH2:8][CH2:7][N:6]([C:10]3[C:11]4[CH:18]=[CH:17][NH:16][C:12]=4[N:13]=[CH:14][N:15]=3)[CH2:5]2)[CH2:3][CH2:2]1)[CH2:27][C:28]#[N:29]Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
An optically-active compound of 4-(1,6-diazaspiro[3.5]non-6-yl)-7H-pyrrolo[2,3-d]pyrimidine (1.55 g) was mixed with 1-cyanoacetyl-3,5-dimethylpyrazole (1.56 g), N,N-diisopropylethylamine (1.66 ml) and 1,4-dioxane (31 ml), and the mixture was heated to 100° C. to stir for 2 hours. The mixture was cooled to room temperature. Then, thereto was added saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/methanol=20/1 to 9/1) to give the titled compound (1.50 g).
Aufarbeitung
- temperatureThe mixture was cooled to room temperature
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated aqueous sodium chloride solution
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/methanol=20/1 to 9/1)
Quellen und Nachweise
- ORD-Eintrag
- ord-58f2e54c222243958a8c7da694e55089
- Quelldatensatz
- uspto-grants-2013_12
- Patentnummer
- US08609647B2
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