Sodium Hydroxide → HCID 57772003, compound

HRID 1661922Notes

Reaction equation

HRID 1661922 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:35][CH3:36])=[CH:20][C:21]([CH:23](OS(C)(=O)=O)[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)=[CH:22][C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].[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:35][CH3:36])=[CH:20][C:21]([CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)=[CH:22][C:12]=3[N:11]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57772049HCID 57772049, compound

Product 1

HCID 57772003HCID 57772003, compoundYield 19.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ca. 250 mg of methanesulfonic acid [2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-pyridin-2-yl-methyl ester in 7 ml THF, 50 mg LiAlH4 are added. The mixture is heated to reflux temperature and stirred for 3 h. After that the reaction mixture is allowed to cool to room temperature and 1N NaOH solution is added and this mixture is stirred for 30 min and filtered. The filtrate is extracted with ethyl acetate (3×). The combined organic layers are washed with water (2×) and brine, dried over MgSO4, filtered and the filtrate is concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (CH2Cl2:MeOH=95:5) to afford 40 mg of the title compound as an oil.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux temperature
  3. stirringthis mixture is stirred for 30 min
  4. filtrationfiltered
  5. extractionThe filtrate is extracted with ethyl acetate (3×)
  6. washThe combined organic layers are washed with water (2×) and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationthe filtrate is concentrated in vacuo
  10. customThe residue is purified by flash-chromatography on silica gel (CH2Cl2:MeOH=95:5)

Sources & evidence

ORD record
ord-d5a8fe5c57bd4199818b2c9d9d14b063
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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