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 1986378노트

반응식

HRID 1986378 반응식
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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-2ad0a16533444ed3aa6b77ee1ff535cd
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07547779B2

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