tert-Butyl 1-[4-(aminocarbonyl)-6-chloropyridin-2-yl]piperidin-4-ylcarbamate → tert-Butyl {1-[4-(aminocarbonyl)-6-cyanopyridin-2-yl]piperidin-4-yl}carbamate

HRID 2233838Notizen

Reaktionsgleichung

[NH2:1][C:2]([C:4]1[CH:9]=[C:8](Cl)[N:7]=[C:6]([N:11]2[CH2:16][CH2:15][CH:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:13][CH2:12]2)[CH:5]=1)=[O:3].[Cu](C#N)[C:26]#[N:27]>O1CCOCC1.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[NH2:1][C:2]([C:4]1[CH:9]=[C:8]([C:26]#[N:27])[N:7]=[C:6]([N:11]2[CH2:16][CH2:15][CH:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:13][CH2:12]2)[CH:5]=1)=[O:3]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

tert-Butyl {1-[4-(aminocarbonyl)-6-chloropyridin-2-yl]piperidin-4-yl}carbamate (Intermediate 16) (100 mg, 0.282 mmol), copper cyanide (101 mg, 1.13 mmol), Pd(dba) (103 mg, 0.11 mmol) and Dppf (250 mg, 0.45 mmol) were placed in anhydrous dioxane (5 ml) under argon. The mixture was heated at 100° C. for 5 h, then diluted with EtOAc (20 ml) and filtered through celite. The mixture was washed with sodium bicarbonate (2×20 ml), brine (20 ml), dried over sodium sulphate and concentrated in vacuo. The brown residue was purified by flash chromatography eluting with DCM and MeOH mixtures to give the title compound as a brown solid (61 mg).

Aufarbeitung

filtrationfiltered through celite
washThe mixture was washed with sodium bicarbonate (2×20 ml), brine (20 ml)
dry with materialdried over sodium sulphate
concentrationconcentrated in vacuo
customThe brown residue was purified by flash chromatography
washeluting with DCM and MeOH mixtures

Quellen und Nachweise

ORD-Eintrag: ord-61e577fc18c04c1c81f1615972b4378d
Quelldatensatz: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07709503B2

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