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Nitrobenzene → 5-(2-cyano-phenoxy)-2-pyridin-2-yl-6-(6-methanesulfonyl-pyridin-3-yloxy)-1H-benzimidazole

HRID 13294
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HRID 13294 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.[N+](C1C=CC=CC=1)([O-])=O.[C:18]([C:20]1[CH:45]=[CH:44][CH:43]=[CH:42][C:21]=1[O:22][C:23]1[CH:24]=[C:25]([NH2:41])[C:26]([NH2:40])=[CH:27][C:28]=1[O:29][C:30]1[CH:31]=[N:32][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:34][CH:35]=1)#[N:19]>CO>[C:18]([C:20]1[CH:45]=[CH:44][CH:43]=[CH:42][C:21]=1[O:22][C:23]1[C:28]([O:29][C:30]2[CH:31]=[N:32][C:33]([S:36]([CH3:39])(=[O:37])=[O:38])=[CH:34][CH:35]=2)=[CH:27][C:26]2[NH:40][C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[N:41][C:25]=2[CH:24]=1)#[N:19]
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참가 물질

5

반응물 3

HCID 7416NitrobenzeneHCID 142732-PyridinecarboxaldehydeHCID 231453124-(2-Cyano-phenoxy)-5-(6-methanesulfonyl-pyridin-3-yloxy)-benzene-1,2-diamine

생성물 1

HCID 231453935-(2-cyano-phenoxy)-2-pyridin-2-yl-6-(6-methanesulfonyl-pyridin-3-yloxy)-1H-benzimidazole

시약·촉매·용매 1

HCID 887Methanol용매

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온도
120 °C

실험 절차

0.007 ml of pyridine-2-carboxaldehyde and 0.5 ml of nitrobenzene were added to a methanol (1 ml) solution of 37 mg of 4-(2-cyano-phenoxy)-5-(6-methanesulfonyl-pyridin-3-yloxy)-benzene-1,2-diamine obtained in (step 5), and the reaction liquid was stirred overnight at 120° C. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=20/1) and through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=15/1) to obtain the entitled compound as a brown solid.

후처리

  1. customobtained in (step 5)
  2. customthe reaction liquid
  3. customThe solvent was evaporated away under reduced pressure
  4. customthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=20/1)
  5. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=15/1)

출처 및 근거

ORD 기록
ord-647fd0ff4e4f4603b26ae8c5067a9f1b
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07728025B2

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