1,10-Phenanthroline → 1-(3-{[2-(4-Amino-furazan-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin-6-yl]oxy}phenyl)ethanone

HRID 1986378Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1986378
Br[C:2]1[N:7]=[CH:6][C:5]2[N:8]=[C:9]([C:13]3[C:14]([NH2:18])=[N:15][O:16][N:17]=3)[N:10]([CH2:11][CH3:12])[C:4]=2[CH:3]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[OH:33][C:34]1[CH:35]=[C:36]([C:40](=[O:42])[CH3:41])[CH:37]=[CH:38][CH:39]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.[Cu](I)I>[NH2:18][C:14]1[C:13]([C:9]2[N:10]([CH2:11][CH3:12])[C:4]3[CH:3]=[C:2]([O:33][C:34]4[CH:35]=[C:36]([C:40](=[O:42])[CH3:41])[CH:37]=[CH:38][CH:39]=4)[N:7]=[CH:6][C:5]=3[N:8]=2)=[N:17][O:16][N:15]=1

Komponenten

8

Edukt 4

HCID 13181,10-PhenanthrolineHCID 84873-HydroxyacetophenoneHCID 10796Cesium carbonateHCID 160998514-(6-Bromo-1-Ethyl-1h-Imidazo[4,5-C]pyridin-2-Yl)-1,2,5-Oxadiazol-3-Amine

Produkt 1

HCID 117729071-(3-{[2-(4-Amino-furazan-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin-6-yl]oxy}phenyl)ethanoneAusbeute 55,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Under nitrogen, a suspension of the product from Example 9, Step 2 (42.7 mg, 138 μmol) in toluene (10 mL) was treated with copper iodide (26.3 mg, 138 μmol), 1,10-phenanthroline (45 mg, 245 μmol), 1-(3-hydroxyphenyl)ethanone (28.2 mg, 207 μmol), and cesium carbonate (90 mg, 276 μmol). This mixture was then heated to reflux for 36 h. After cooling to rt, the reaction mixture was diluted with ethyl acetate (50 ml), filtered through a celite pad and then the filtrate was concentrated in vacuo. The residue was purified by reverse phase HPLC to give the title compound (28.1 mg, 43%). MS (ES+) m/e 365 [M+H]+.

Aufarbeitung

  1. temperatureThis mixture was then heated
  2. temperatureto reflux for 36 h
  3. filtrationfiltered through a celite pad
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-2ad0a16533444ed3aa6b77ee1ff535cd
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07547779B2

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