Water → 9-(4-{[3-(2-Methoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]oxy}phenyl)-9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridine

HRID 572185노트

반응식

HRID 572185 반응식
[N:1]1[CH:2]=[CH:3][N:4]2[C:12]3[C:7](=[N:8][CH:9]=[CH:10][CH:11]=3)[N:6]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[C:5]=12.[H-].[Na+].[CH3:22][O:23][CH2:24][CH2:25][N:26]1[C:30]2=[N:31][CH:32]=[CH:33][CH:34]=[C:29]2[N:28]=[C:27]1S(C)(=O)=O.O>CN(C=O)C>[CH3:22][O:23][CH2:24][CH2:25][N:26]1[C:30]2=[N:31][CH:32]=[CH:33][CH:34]=[C:29]2[N:28]=[C:27]1[O:19][C:16]1[CH:17]=[CH:18][C:13]([N:6]2[C:7]3=[N:8][CH:9]=[CH:10][CH:11]=[C:12]3[N:4]3[CH:3]=[CH:2][N:1]=[C:5]23)=[CH:14][CH:15]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 667277733-(2-methoxyethyl)-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridineHCID 867049864-(9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridin-9-yl)phenol

생성물 1

HCID 602024079-(4-{[3-(2-Methoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]oxy}phenyl)-9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of 4-(9H-imidazo[1′,2′:1,2]imidazo[4,5-b]pyridin-9-yl)phenol (175 mg) obtained in Example 9, step C) in DMF (2 ml) was added sodium hydride (60% in oil, 30 mg) at room temperature by small portions. After stirring for 10 min, a solution of 3-(2-methoxyethyl)-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine[191 mg) in DMF (2 ml) was added, and the obtained mixture was stirred under microwave irradiation at 180° C. for 30 min. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/THF) and recrystallized from ethanol to give the title compound (198 mg).

후처리

  1. stirringthe obtained mixture was stirred under microwave irradiation at 180° C. for 30 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/THF)
  7. customrecrystallized from ethanol

출처 및 근거

ORD 기록
ord-b567a040aca54573b1f99111a3dda01d
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029388B2

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