Methanol → C-[2-(4-Isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-methylamine

HRID 1661940Notes

Reaction equation

HRID 1661940 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]3[C:19]([O:25][CH3:26])=[CH:20][C:21]([C:23]#[N:24])=[CH:22][C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].CO.[OH-].[Na+]>C1COCC1>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]3[C:19]([O:25][CH3:26])=[CH:20][C:21]([CH2:23][NH2:24])=[CH:22][C:12]=3[N:11]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 112795222-(4-Isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 57772089C-[2-(4-Isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-methylamineYield 59.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 100 mg (0.286 mmol) 2-(4-Isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carbonitrile in 4 ml THF, LiAlH4 (54 mg, 1.43 mmol) is added. The reaction mixture is stirred at reflux temperature for 2 h. After that methanol (0.5 ml) and 5 ml 15% NaOH-solution is added. This mixture is filtered and the filtrate is extracted (3×) with EtOAc. The combined organic layers are washed with water (2×) and brine, dried over MgSO4, filtered and concentrated in vacuo to afford 60 mg of the title compound as an oil.

Workup

  1. temperatureat reflux temperature for 2 h
  2. filtrationThis mixture is filtered
  3. extractionthe filtrate is extracted (3×) with EtOAc
  4. washThe combined organic layers are washed with water (2×) and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ada12d51a66541cab818efe7663c8438
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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