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

HRID 1454721
Notes
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Reaction equation

HRID 1454721 reaction equation
C([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[CH:19]=[C:18]([Cl:20])[C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=2[NH:25][C:26](=O)[CH2:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)=[CH:9][CH:8]=1)(=O)C.[OH-].[Na+]>C(O)C>[Cl:20][C:18]1[C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]2[N:25]=[C:26]([CH2:27][CH2:28][CH2:29][C:30]3[CH:31]=[CH:32][N:33]=[CH:34][CH:35]=3)[N:13]([C:10]3[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][OH:4])=[CH:8][CH:9]=3)[C:14]=2[CH:19]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 218764332-(4-{[5-Chloro-2-{[4-(4-pyridinyl)butanoyl]amino}-4-(trifluoromethyl)phenyl]amino}phenyl)ethyl acetate

Product 1

HCID 218765222-{4-[6-chloro-2-[3-(4-pyridinyl)propyl]-5-(trifluoromethyl)-1H-benzimidazol-1-yl]phenyl}ethanolYield 54.4%

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-f4f26981a9de4612800fd056f3facabe
Source dataset
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07479564B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes