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Sodium Hydroxide → 2-{4-[6-chloro-2-[3-(4-pyridinyl)propyl]-5-(trifluoromethyl)-1H-benzimidazol-1-yl]phenyl}ethanol

HRID 858531
Notes
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Reaction equation

HRID 858531 reaction equation
[Cl:1][C:2]1[C:3]([C:42]([F:45])([F:44])[F:43])=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[N:7]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH2:26]N(S(C4C=CC(C)=CC=4)(=O)=O)C(=O)[O-])=[CH:21][CH:20]=3)[C:6]=2[CH:41]=1.[OH-:46].[Na+]>C(O)C>[Cl:1][C:2]1[C:3]([C:42]([F:43])([F:44])[F:45])=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[N:7]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][OH:46])=[CH:21][CH:20]=3)[C:6]=2[CH:41]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 218762802-{4-[6-Chloro-2-[3-(4pyridinyl)propyl]-5-(trifluoromethyl)-1H-benzimidazol-1-YL]phenyl}ethyl(4-methylphenyl)sulfonylcarbamate

Product 1

HCID 218765222-{4-[6-chloro-2-[3-(4-pyridinyl)propyl]-5-(trifluoromethyl)-1H-benzimidazol-1-yl]phenyl}ethanolYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 2-(4-{[5-chloro-2-{[4-(4-pyridinyl)butanoyl]amino}-4-(trifluoromethyl)phenyl]amino}phenyl)ethyl acetate (step 3, 220 mg, 0.42 mmol) and 2N NaOH (15 ml) in ethanol (20 ml) was stirred at 40° C. for 7 h. The solvent was removed and the residue was added water (50 ml). The mixture was extracted with ethyl acetate(100 ml). The organic layer was washed with brine (50 ml), then dried (Na2SO4). After removal of solvent, the crude product was purified by flash column chromatography eluting with dichloromethane:methanol (20:1) to afford 105 mg (54%) of the title compound as pale brown oil.

Workup

  1. customThe solvent was removed
  2. additionthe residue was added water (50 ml)
  3. extractionThe mixture was extracted with ethyl acetate(100 ml)
  4. washThe organic layer was washed with brine (50 ml)
  5. dry with materialdried (Na2SO4)
  6. customAfter removal of solvent
  7. customthe crude product was purified by flash column chromatography
  8. washeluting with dichloromethane:methanol (20:1)

Sources & evidence

ORD record
ord-407e7ee4cc3a451d9de554bc43508324
Source dataset
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07148234B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes