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 1986378Notes

Reaction equation

HRID 1986378 reaction equation
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

Participants

8

Reactant 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

Product 1

HCID 117729071-(3-{[2-(4-Amino-furazan-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin-6-yl]oxy}phenyl)ethanoneYield 55.9%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-2ad0a16533444ed3aa6b77ee1ff535cd
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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