Sodium Hydroxide → 2-(2-chloro-5-{[(tert-butoxycarbonyl)-amino]-methyl}-phenylamino)-6-(2,2-difluoro-ethoxy)-1-methyl-1H-benzimidazole-5-carboxylic acid

HRID 1410244Notes

Reaction equation

HRID 1410244 reaction equation
C([O:3][C:4]([C:6]1[C:32]([O:33][CH2:34][CH:35]([F:37])[F:36])=[CH:31][C:9]2[N:10]([CH3:30])[C:11]([NH:13][C:14]3[CH:19]=[C:18]([CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:17]=[CH:16][C:15]=3[Cl:29])=[N:12][C:8]=2[CH:7]=1)=[O:5])C.[OH-].[Na+]>O1CCOCC1>[Cl:29][C:15]1[CH:16]=[CH:17][C:18]([CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:19][C:14]=1[NH:13][C:11]1[N:10]([CH3:30])[C:9]2[CH:31]=[C:32]([O:33][CH2:34][CH:35]([F:37])[F:36])[C:6]([C:4]([OH:5])=[O:3])=[CH:7][C:8]=2[N:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86646338Ethyl-2-(2-chloro-5-{[(tert-butoxycarbonyl)-amino]-methyl}-phenylamino)-6-(2,2-difluoro-ethoxy)-1-methyl-1H-benzimidazole-5-carboxylate

Product 1

HCID 866463402-(2-chloro-5-{[(tert-butoxycarbonyl)-amino]-methyl}-phenylamino)-6-(2,2-difluoro-ethoxy)-1-methyl-1H-benzimidazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of ethyl-2-(2-chloro-5-{[(tert-butoxycarbonyl)-amino]-methyl}-phenylamino)-6-(2,2-difluoro-ethoxy)-1-methyl-1H-benzimidazole-5-carboxylate (1.35 g; 2.50 mmol), NaOH (4 mL; 2 M aq; 8 mmol) and 1,4-dioxane (15 mL) was refluxed for 3 h. After cooling to rt the mixture was acidified to pH ˜5-6 and extracted with EtOAc. The organic extracts were dried over Na2SO4, filtered and concentrated. The residue was washed with Et2O to give the sub-title compound. Yield: 1.12 g (88%).

Workup

  1. temperaturewas refluxed for 3 h
  2. extractionextracted with EtOAc
  3. dry with materialThe organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washThe residue was washed with Et2O

Sources & evidence

ORD record
ord-b6946a3386644b148b810e5b2250ca10
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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