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 1986378ノート

反応式

HRID 1986378 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-2ad0a16533444ed3aa6b77ee1ff535cd
出典データセット
uspto-grants-2009_06
特許番号
US07547779B2

反応ノート

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