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Water → HCID 66728069, Verbindung

HRID 573334
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 573334
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]=[C:3]1S(C)(=O)=O.[CH3:15][CH:16]([N:18]1[C:26]2[C:21](=[N:22][CH:23]=[CH:24][CH:25]=2)[C:20]([C:27]2[C:32](O)=[CH:31][CH:30]=[CH:29][N:28]=2)=[N:19]1)[CH3:17].[H-].[Na+].[OH2:36]>CN(C=O)C>[CH3:15][CH:16]([N:18]1[C:26]2[C:21](=[N:22][CH:23]=[CH:24][CH:25]=2)[C:20]([C:27]2[CH:32]=[CH:31][C:30]([O:36][C:3]3[N:2]([CH3:1])[C:6]4=[N:7][CH:8]=[CH:9][CH:10]=[C:5]4[N:4]=3)=[CH:29][N:28]=2)=[N:19]1)[CH3:17]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 585773713-Methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridineHCID 136409090HCID 136409090, Verbindung

Produkt 1

HCID 66728069HCID 66728069, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of 3-methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine (174 mg) and 6-[(1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridin-3-yl]pyridin-3-ol (140 mg) in DMF (1.5 ml) was added NaH (60% in oil, 35.2 mg), and the mixture was stirred at 100° C. for 1 h. The mixture was heated at 180° C. for 30 min under microwave irradiation. The mixture was poured into water and extracted with AcOEt. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (AcOEt/hexane) and silica gel column chromatography (AcOEt/hexane). The eluent was evaporated and the residue was purified by preparative HPLC (C18, eluent: H2O/CH3CN (10 mM NH4HCO3)). The eluent was evaporated to give the title compound (68.1 mg).

Aufarbeitung

  1. temperatureThe mixture was heated at 180° C. for 30 min under microwave irradiation
  2. extractionextracted with AcOEt
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (AcOEt/hexane) and silica gel column chromatography (AcOEt/hexane)
  8. customThe eluent was evaporated
  9. customthe residue was purified by preparative HPLC (C18, eluent: H2O/CH3CN (10 mM NH4HCO3))
  10. customThe eluent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-201c0c5494724204afa2f4c414acd520
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09029536B2

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