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

HRID 13294
Notes
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Reaction equation

HRID 13294 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887Methanol
Solvent

Conditions

Temperature
120 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-647fd0ff4e4f4603b26ae8c5067a9f1b
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07728025B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes