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 28A) and 1.89 g (14.7 mmol) of diisopropylethylamine were suspended in 6 ml of DMSO and heated in a microwave reactor at 130° C. for 8 h. The reaction mixture was diluted with ethyl acetate (100 ml) and water (40 ml), and the organic phase was separated off and washed with saturated aqueous sodium chloride solution (50 ml), dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1 to 1:1). This gave 2.04 g (60% of theory) of the product as a solid.
Aufarbeitung
- customthe organic phase was separated off
- washwashed with saturated aqueous sodium chloride solution (50 ml)
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- customThe residue was chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1 to 1:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-7a31d3b9d4ff4565979b615fef97de39
- Quelldatensatz
- uspto-grants-2013_07
- Patentnummer
- US08476267B2
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