Sodium hydride → Dimethylethyl 5-[5,6-dihydro-5-oxo-pyrido[2',1':2,3]imidazo[4,5-c]isoquinolin-6-yl]-alpha-cyano-2-pyridineacetate

HRID 1670696

Reaktionsgleichung

Reaktionsgleichung von HRID 1670696
[H-].[Na+].[C:3]([CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])#[N:4].Br[C:14]1[N:19]=[CH:18][C:17]([N:20]2[C:29]3[N:30]4[CH:36]=[CH:35][CH:34]=[CH:33][C:31]4=[N:32][C:28]=3[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]2=[O:37])=[CH:16][CH:15]=1>N1C=CC=CC=1>[O:37]=[C:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:28]2[N:32]=[C:31]3[CH:33]=[CH:34][CH:35]=[CH:36][N:30]3[C:29]=2[N:20]1[C:17]1[CH:16]=[CH:15][C:14]([CH:5]([C:3]#[N:4])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[N:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 70693tert-Butyl cyanoacetateHCID 247710936-(6-bromo-pyridin-3-yl)-pyrido-[2',1':2,3]imidazo[4,5-c]isoquinolin-5(6H)-one

Produkt 1

HCID 57767017Dimethylethyl 5-[5,6-dihydro-5-oxo-pyrido[2',1':2,3]imidazo[4,5-c]isoquinolin-6-yl]-alpha-cyano-2-pyridineacetateAusbeute 45,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Sodium hydride (2.2 equiv., 0.844 mmol, 0.034 g (60%)) was added to a solution of tert-butyl cyanoacetate (1.2 equiv., 0.460 mmol, 0.065 g) in dry pyridine (1 ml) under Ar atmosphere. The catalyst—prepared as described above—was injected, and the mixture was stirred at room temperature for 5 min. Compound 21 (1.0 equiv., 0.383 mmol, 0.150 g) was then added and the reaction mixture was heated at 85° C. for 2 h. After destruction of excess sodium hydride with methanol, the solvent was concentrated under vacuum. The residue was purified by column chromatography (dichloromethane/methanol (7M NH3) 95:5) to give dimethylethyl 5-[5,6-dihydro-5-oxo-pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-6-yl]-α-cyano-2-pyridineacetate (I12) (0.078 g, yield=45%).

Aufarbeitung

  1. customThe catalyst—prepared
  2. temperaturethe reaction mixture was heated at 85° C. for 2 h
  3. customAfter destruction of excess sodium hydride with methanol
  4. concentrationthe solvent was concentrated under vacuum
  5. customThe residue was purified by column chromatography (dichloromethane/methanol (7M NH3) 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-a2c226f23be34d9798213832d6da0b31
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07994187B2

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