3-{4-Chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazol-7-yl}-2,4-dimethylpentan-3-ol → 4-Chloro-N-(4-chloro-2-methoxy-6-methylphenyl)-7-(1-isopropyl-2-methylprop-1-en-1-yl)-1-methyl-1H-benzimidazol-2-amine

HRID 1698582Notes

Reaction equation

HRID 1698582 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]3[C:17]([CH3:18])=[CH:16][C:15]([Cl:19])=[CH:14][C:13]=3[O:20][CH3:21])[N:7]([CH3:22])[C:6]=2[C:5]([C:23](O)([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]3[C:17]([CH3:18])=[CH:16][C:15]([Cl:19])=[CH:14][C:13]=3[O:20][CH3:21])[N:7]([CH3:22])[C:6]=2[C:5]([C:23]([CH:27]([CH3:29])[CH3:28])=[C:24]([CH3:25])[CH3:26])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 580123753-{4-Chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazol-7-yl}-2,4-dimethylpentan-3-ol

Product 1

HCID 580123454-Chloro-N-(4-chloro-2-methoxy-6-methylphenyl)-7-(1-isopropyl-2-methylprop-1-en-1-yl)-1-methyl-1H-benzimidazol-2-amineYield 80%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3-{4-chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazol-7-yl}-2,4-dimethylpentan-3-ol (75 mg, 0.17 mmol) in trifluoroacetic acid (3 mL) was heated at 70° C. for 1 h. After cooling, the reaction mixture was concentrated in vacuo, neutralized with saturated sodium hydrogen carbonate, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative HPLC eluting with a 5-95% acetonitrile/water gradient mixture to give the title compound (58 mg, 80%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative HPLC
  8. washeluting with a 5-95% acetonitrile/water gradient mixture

Sources & evidence

ORD record
ord-b79a3bd311644e8fb4288f3519beed6c
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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