Water → HCID 178428401, compound

HRID 13244Notes

Reaction equation

HRID 13244 reaction equation
[OH:1]OS([O-])=O.[K+].[OH2:7].[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[C:30]([O:31][C:32]3[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=3)=[CH:29][C:19]3[NH:20][C:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=4)=[N:22][C:18]=3[CH:17]=2)=[CH:11][N:10]=1>O1CCCC1>[CH3:14][C:13]1[CH:8]=[CH:9][N:10]=[CH:11][C:12]=1[S:15]([C:16]1[C:30]([O:31][C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)=[CH:29][C:19]2[NH:20][C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[N:22][C:18]=2[CH:17]=1)(=[O:1])=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 23145144HCID 23145144, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 178428401HCID 178428401, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

92 mg of OXONE and 0.1 ml of water were added to a tetrahydrofuran (1.5 ml) solution of 42 mg of 5-(2-methyl-pyridin-5-ylsulfanyl)-2-pyridin-2-yl-6-(pyridin-3-yloxy)-1H-benzimidazole obtained in Example 13, and the reaction liquid was stirred overnight at room temperature. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]. An aqueous solution of saturated sodium hydrogencarbonate was added to the resulting fraction, and this was extracted with chloroform, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure to obtain the entitled compound.

Workup

  1. customthe reaction liquid
  2. customThe solvent was evaporated away under reduced pressure
  3. customthe resulting residue was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]
  4. additionAn aqueous solution of saturated sodium hydrogencarbonate was added to the resulting fraction
  5. extractionthis was extracted with chloroform
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe solvent was evaporated away under reduced pressure
  8. customto obtain the entitled compound

Sources & evidence

ORD record
ord-931c24eaee15424d8930ca980c16fce4
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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