Diethyl Ether → 3-{4-Chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazol-7-yl}-2,2,4,4-tetramethylpentan-3-ol

HRID 1698580Notes

Reaction equation

HRID 1698580 reaction equation
CC[CH2:3][CH2:4][CH3:5].[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]([O:35]C)=O)=[CH:14][CH:13]=1.[CH2:37](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]([OH:35])([C:4]([CH3:3])([CH3:5])[CH3:37])[C:6]([CH3:9])([CH3:8])[CH3:7])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8003PentaneHCID 67273388Methyl 4-chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazole-7-carboxylateHCID 178418306HCID 178418306, compound

Product 1

HCID 580123123-{4-Chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazol-7-yl}-2,2,4,4-tetramethylpentan-3-olYield 5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 were dried over magnesium sulfate, filtered, and concentrated in vacuo to give 5 mg (0.010 mmol, 5%) 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 were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-037c2eac36724987856f4c60928d8f71
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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