Sodium hydride → tert-Butyl [3-(2-methoxy-2-oxoethyl)-4,6-dimethyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetate

HRID 1921178Notes

Reaction equation

HRID 1921178 reaction equation
[CH3:1][C:2]1[C:10]2[NH:9][C:8](=[O:11])[N:7]([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:6]=2[CH:5]=[C:4]([CH3:20])[CH:3]=1.[H-].[Na+].Br[CH2:24][C:25]([O:27][CH3:28])=[O:26]>CN(C=O)C>[CH3:28][O:27][C:25](=[O:26])[CH2:24][N:9]1[C:10]2[C:2]([CH3:1])=[CH:3][C:4]([CH3:20])=[CH:5][C:6]=2[N:7]([CH2:12][C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[C:8]1=[O:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 86607783tert-Butyl (4,6-dimethyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)acetate

Product 1

HCID 86607784tert-Butyl [3-(2-methoxy-2-oxoethyl)-4,6-dimethyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl (4,6-dimethyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)acetate from Step B (100 mg, 0.36 mmol) in DMF (3 mL) was added sodium hydride (17 mg of a 60% dispersion in mineral oil, 0.43 mmol) followed by methyl bromoacetate (0.041 mL, 0.43 mmol) and the reaction mixture was stirred for 2 h. The reaction was purified directly by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. Lyophilization of the product-containing fractions afforded the title compound. MS: m/z=349 (M+1).

Workup

  1. customThe reaction was purified directly by HPLC
  2. washeluting with a gradient of H2O

Sources & evidence

ORD record
ord-7519edd016434ca99edbbdc4fa46f933
Source dataset
uspto-grants-2012_05
Patent number
US08173655B2

Reaction notes

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