Sulfuric Acid → 5-(2-Carbamoyl-phenoxy)-2-pyridin-2-yl-6-(pyridin-3-yloxy)-1H-benzimidazole

HRID 13241Notes

Reaction equation

HRID 13241 reaction equation
S(=O)(=O)(O)[OH:2].[C:6]([C:8]1[CH:36]=[CH:35][CH:34]=[CH:33][C:9]=1[O:10][C:11]1[C:25]([O:26][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)=[CH:24][C:14]2[NH:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[N:17][C:13]=2[CH:12]=1)#[N:7]>>[C:6]([C:8]1[CH:36]=[CH:35][CH:34]=[CH:33][C:9]=1[O:10][C:11]1[C:25]([O:26][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)=[CH:24][C:14]2[NH:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[N:17][C:13]=2[CH:12]=1)(=[O:2])[NH2:7]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 231456625-(2-Cyano-phenoxy)-2-pyridin-2-yl-6-(pyridin-3-yloxy)-1H-benzimidazole

Product 1

HCID 231458315-(2-Carbamoyl-phenoxy)-2-pyridin-2-yl-6-(pyridin-3-yloxy)-1H-benzimidazole

Procedure

A 80% sulfuric acid solution of 3.5 mg of 5-(2-cyano-phenoxy)-2-pyridin-2-yl-6-(pyridin-3-yloxy)-1H-benzimidazole obtained in Example 5 was stirred overnight at 50° C. The reaction mixture was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]. The solvent of the resulting fraction was evaporated away under reduced pressure to obtain the entitled compound as a colorless solid.

Workup

  1. customThe reaction mixture was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]
  2. customThe solvent of the resulting fraction was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-3476d846d1274633b811b2342e0b7f20
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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