Dimethylformamide → HCID 67142201, Verbindung

HRID 1932395Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1932395
[Cl:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[CH2:5][N:6]1[C:10]2=[C:11]([N:20]3[CH2:29][CH2:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21]3)[N:12]=[C:13]([C:15]3[NH:19][N:18]=[N:17][N:16]=3)[CH:14]=[C:9]2[C:8]([CH3:30])=[C:7]1[CH3:31].[C:35](=O)([O-])[O-].[K+].[K+].CN(C)C=O.IC>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[CH2:5][N:6]1[C:10]2=[C:11]([N:20]3[CH2:29][CH2:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21]3)[N:12]=[C:13]([C:15]3[N:19]([CH3:35])[N:18]=[N:17][N:16]=3)[CH:14]=[C:9]2[C:8]([CH3:30])=[C:7]1[CH3:31]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178428440HCID 178428440, Verbindung

Produkt 1

HCID 67142201HCID 67142201, VerbindungAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

2-[1-(3-Chlorobenzyl)-2,3-dimethyl-5-(1H-tetrazol-5-yl)-1H-pyrrolo[2,3-c]pyridin-7-yl]-1,2,3,4-tetrahydroisoquinoline (50 mg, 0.11 mmol) prepared in Example 852 and potassium carbonate (22.1 mg, 0.16 mmol) were dripped into anhydrous N,N-dimethylformamide (1 ml). Iodomethane (10 μl, 0.16 mmol) was added to the reaction mixture, which was then stirred overnight at room temperature. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/3, v/v) to give 18 mg of the titled compound as a white solid (Yield: 34%).

Aufarbeitung

  1. extractionwas then extracted with ethyl acetate
  2. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/3

Quellen und Nachweise

ORD-Eintrag
ord-f038f47cf3cc4f9b8c4ebdaf1aa80d3b
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188114B2

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