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Pentane → 1-{4-Chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazol-7-yl}-2,2-dimethylpropan-1-one

HRID 1698579
Notes
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Reaction equation

HRID 1698579 reaction equation
CCCCC.[C:6]([Li])([CH3:9])([CH3:8])[CH3:7].[Cl:11][C:12]1[C:20]2[N:19]=[C:18]([NH:21][C:22]3[C:27]([CH3:28])=[CH:26][C:25]([Cl:29])=[CH:24][C:23]=3[O:30][CH3:31])[N:17]([CH3:32])[C:16]=2[C:15]([C:33](OC)=[O:34])=[CH:14][CH:13]=1>C(OCC)C.O>[Cl:11][C:12]1[C:20]2[N:19]=[C:18]([NH:21][C:22]3[C:27]([CH3:28])=[CH:26][C:25]([Cl:29])=[CH:24][C:23]=3[O:30][CH3:31])[N:17]([CH3:32])[C:16]=2[C:15]([C:33](=[O:34])[C:6]([CH3:9])([CH3:8])[CH3:7])=[CH:14][CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8003PentaneHCID 67273388Methyl 4-chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazole-7-carboxylateHCID 178418306HCID 178418306, compound

Product 1

HCID 580123821-{4-Chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazol-7-yl}-2,2-dimethylpropan-1-one

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 3283Diethyl EtherSolvent

Procedure

A n-pentane solution of tert-butyl lithium (1.46 M, 0.5 ml) was added to a solution of methyl 4-chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazole-7-carboxylate (100 mg, 0.23 mmol) in diethyl ether (5 mL) at −78° C. and stirred for 1 h. The reaction mixture was diluted with water (5 mL), stirred at room temperature for 0.5 h and extracted with ethyl acetate. The organics was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative HPLC. The resultant was neutralized with aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organics was dried over magnesium sulfate, filtered, and concentrated in vacuo to give 31 mg (0.073, mmol, 32%) of the title compound.

Workup

  1. stirringstirred at room temperature for 0.5 h
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organics was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative HPLC
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organics was dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6cafd3da58fa49b298ce3936530843a3
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08163935B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes