Cesium carbonate → HCID 58577309, Verbindung

HRID 82561

Reaktionsgleichung

Reaktionsgleichung von HRID 82561
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]3[C:14]4=[N:15][CH:16]=[CH:17][CH:18]=[C:13]4[N:12]([CH2:19][CH3:20])[C:11]3=[O:21])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Cl[C:23]1[S:24][CH:25]=[CH:26][N:27]=1.C([O-])([O-])=O.[Cs+].[Cs+].C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:19]([N:12]1[C:13]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[N:10]([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[N:1]([C:23]2[S:24][CH:25]=[CH:26][N:27]=2)[CH:2]=[CH:3]3)[C:11]1=[O:21])[CH3:20]

Komponenten

6

Edukt 4

HCID 10796Cesium carbonateHCID 764292-ChlorothiazoleHCID 516892Sodium BicarbonateHCID 585772823-(2,3-dihydro-1H-indol-5-yl)-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Produkt 1

HCID 58577309HCID 58577309, VerbindungAusbeute 27,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 3-(2,3-dihydro-1H-indol-5-yl)-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (75 mg), 2-chlorothiazole (48.0 mg) and Cs2CO3 (174 mg) in DMF (3 mL) was stirred at 100° C. for 3 days, treated with saturated NaHCO3 solution, and extracted with AcOEt. The organic layer was separated, dried over MgSO4 and concentrated in vacuo. The residue was purified by prep. HPLC and crystallized from AcOEt/Hexane to give the title compound as white crystals (27.0 mg).

Aufarbeitung

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by prep
  6. customHPLC and crystallized from AcOEt/Hexane

Quellen und Nachweise

ORD-Eintrag
ord-a616ade2b40049af96929bb3f057c80d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846713B2

Verknüpfte Notizen

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