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Water → 1-{2-[4-(9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridin-9-yl)phenoxy]-1H-benzimidazol-1-yl}propan-2-one

HRID 572181
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HRID 572181 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+].Cl[C:23]1[N:27]([CH2:28][C:29](=[O:31])[CH3:30])[C:26]2[CH:32]=[CH:33][CH:34]=[CH:35][C:25]=2[N:24]=1.O>CN(C=O)C>[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]([O:19][C:23]4[N:27]([CH2:28][C:29](=[O:31])[CH3:30])[C:26]5[CH:32]=[CH:33][CH:34]=[CH:35][C:25]=5[N:24]=4)=[CH:15][CH:14]=3)[C:5]=12
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 122342441-(2-Chloro-1H-benzimidazol-1-yl)propan-2-oneHCID 867049864-(9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridin-9-yl)phenol

생성물 1

HCID 867049891-{2-[4-(9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridin-9-yl)phenoxy]-1H-benzimidazol-1-yl}propan-2-one수율 19.4%

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 (1.13 g) obtained in Example 9, step C) in DMF (10 ml) was added sodium hydride (60% in oil, 0.200 g) at room temperature by small portions. After stirring for 10 min, a solution of 1-(2-chloro-1H-benzimidazol-1-yl)propan-2-one (1.25 g) in DMF (5 ml) was added, and the obtained mixture was stirred under microwave irradiation at 180° C. for 1.5 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate) and recrystallized from methanol to give the title compound (0.371 g).

후처리

  1. stirringthe obtained mixture was stirred under microwave irradiation at 180° C. for 1.5 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate)
  7. customrecrystallized from methanol

출처 및 근거

ORD 기록
ord-28d7fd6c615f40f399dd86cd57c9d363
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09029388B2

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