Diisopropylethylamine → Tert-butyl 3-[(6-amino-5-cyanopyridin-2-yl)amino]piperidine-1-carboxylate
Reaktionsgleichung
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[NH2:15][C:16]1[C:21]([C:22]#[N:23])=[CH:20][CH:19]=[C:18](Cl)[N:17]=1.C(N(C(C)C)CC)(C)C>CS(C)=O.C(OCC)(=O)C.O>[NH2:15][C:16]1[N:17]=[C:18]([NH:1][CH:2]2[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]2)[CH:19]=[CH:20][C:21]=1[C:22]#[N:23]Komponenten
7
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 130 °C
Versuchsvorschrift
2.15 g (10.7 mmol) of tert-butyl 3-aminopiperidine-1-carboxylate, 1.50 g (9.77 mmol) of 2-amino-6-chloropyridine-3-carbonitrile (Example 5A) and 1.89 g (14.7 mmol) of diisopropylethylamine were suspended in 6 ml of DMSO and heated to 130° C. in a microwave reactor for 8 h. The reaction mixture was diluted with ethyl acetate (100 ml) and water (40 ml), and the organic phase was removed and washed with saturated aqueous sodium chloride solution (50 ml), dried over magnesium sulphate and concentrated. The residue was chromatographed on silica gel (eluent: cyclohexane/ethyl acetate 4:1 to 1:1). 2.04 g (60% of theory) of the product were isolated in solid form.
Aufarbeitung
- customthe organic phase was removed
- washwashed with saturated aqueous sodium chloride solution (50 ml)
- dry with materialdried over magnesium sulphate
- concentrationconcentrated
- customThe residue was chromatographed on silica gel (eluent: cyclohexane/ethyl acetate 4:1 to 1:1)
- custom2.04 g (60% of theory) of the product were isolated in solid form
Quellen und Nachweise
- ORD-Eintrag
- ord-b0f0c0c08b81410bba1e54a0a4a2dc10
- Quelldatensatz
- uspto-grants-2014_03
- Patentnummer
- US08664246B2
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