2-Mercaptoethanol → 2-(5-((6-(1-Acetylpyrrolidin-2-yl)-2-pyridin-2-yl-1H-benzimidazol-5-yl)oxy)pyridin-2-ylsulfanyl)ethanol

HRID 13417

Reaction equation

HRID 13417 reaction equation
[SH:1][CH2:2][CH2:3][OH:4].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[C:16]([N:19]1[CH2:23][CH2:22][CH2:21][CH:20]1[C:24]1[C:25]([O:39][C:40]2[CH:41]=[N:42][C:43](Cl)=[CH:44][CH:45]=2)=[CH:26][C:27]2[N:31]=[C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)[NH:29][C:28]=2[CH:38]=1)(=[O:18])[CH3:17]>C(=O)(O)[O-].[Na+]>[C:16]([N:19]1[CH2:23][CH2:22][CH2:21][CH:20]1[C:24]1[C:25]([O:39][C:40]2[CH:45]=[CH:44][C:43]([S:1][CH2:2][CH2:3][OH:4])=[N:42][CH:41]=2)=[CH:26][C:27]2[N:31]=[C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)[NH:29][C:28]=2[CH:38]=1)(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 15672-MercaptoethanolHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 231451026-(1-Acetylpyrrolidin-2-yl)-5-((6-chloropyridin-3-yl)oxy)-2-pyridin-2-yl-1H-benzimidazole

Product 1

HCID 231451152-(5-((6-(1-Acetylpyrrolidin-2-yl)-2-pyridin-2-yl-1H-benzimidazol-5-yl)oxy)pyridin-2-ylsulfanyl)ethanol

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
120 °C

Procedure

20 mg of 2-mercaptoethanol and 10 mg of potassium carbonate were added in order to an N,N-dimethylformamide (1 ml) solution of 20 mg of 6-(1-acetylpyrrolidin-2-yl)-5-(6-chloropyridin-3-yl)oxy-2-pyridin-2-yl-1H-benzimidazole obtained in Example 504, and the reaction liquid was stirred at 120° C. for 5 hours. After cooled, the reaction liquid was diluted with aqueous saturated sodium bicarbonate, extracted with chloroform, and the organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1) to obtain the entitled compound as a white solid.

Workup

  1. customthe reaction liquid
  2. temperatureAfter cooled
  3. customthe reaction liquid
  4. extractionextracted with chloroform
  5. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  6. customthe solvent was evaporated away under reduced pressure
  7. customThe resulting residue was purified
  8. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-789f003969094e3887548f5c03ce85d9
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Linked notes

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