Monomethylamine methanol → 5-(4-Methylcarbamoyl-phenoxy)-2-pyridin-2-yl-6-(pyridin-3-yloxy)-1H-benzimidazole

HRID 13242

Reaction equation

HRID 13242 reaction equation
[CH3:1][NH2:2].[CH3:3][OH:4].COC([C:9]1[C:17]2[N:16]=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[NH:14][C:13]=2[CH:12]=[C:11]([O:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[CH:10]=1)=O>CO>[CH3:1][NH:2][C:3]([C:17]1[CH:13]=[CH:12][C:11]([O:24][C:10]2[C:11]([O:24][C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)=[CH:12][C:13]3[NH:14][C:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=4)=[N:16][C:17]=3[CH:9]=2)=[CH:10][CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 57454252Monomethylamine methanolHCID 866192024-methoxycarbonyl-2-pyridin-2-yl-6-(pyridin-3-yloxy)-1H-benzimidazole

Product 1

HCID 231456535-(4-Methylcarbamoyl-phenoxy)-2-pyridin-2-yl-6-(pyridin-3-yloxy)-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.05 ml of a 40% methylamine/methanol solution was added to a methanol (1 ml) solution of 3.0 mg of 5-(4-methoxycarbonyl-2-pyridin-2-yl-6-(pyridin-3-yloxy)-1H-benzimidazole obtained in Example 10, and the reaction liquid was stirred overnight at room temperature. The solvent was evaporated away under reduced pressure, and this was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=20/1) to obtain the entitled compound.

Workup

  1. customthe reaction liquid
  2. customThe solvent was evaporated away under reduced pressure
  3. customthis was purified
  4. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=20/1)
  5. customto obtain the entitled compound

Sources & evidence

ORD record
ord-770324bb1c4145bc8f0102d368437c92
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Linked notes

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