Sodium hydride → HCID 23581783, compound

HRID 1828199Notes

Reaction equation

HRID 1828199 reaction equation
[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[C:13]([C:17]4[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=4)=[N:14][NH:15][CH:16]=3)=[CH:11][C:6]=2[N:5]([CH2:24][CH3:25])[C:4]1=[O:26])[CH3:2].[H-].[Na+].Br[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32].C(=O)(O)[O-].[Na+]>O1CCOCC1>[C:34]([O:33][C:31](=[O:32])[CH2:30][N:15]1[CH:16]=[C:12]([C:10]2[CH:9]=[CH:8][C:7]3[N:3]([CH2:1][CH3:2])[C:4](=[O:26])[N:5]([CH2:24][CH3:25])[C:6]=3[CH:11]=2)[C:13]([C:17]2[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=2)=[N:14]1)([CH3:37])([CH3:36])[CH3:35].[C:34]([O:33][C:31](=[O:32])[CH2:30][N:14]1[C:13]([C:17]2[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=2)=[C:12]([C:10]2[CH:9]=[CH:8][C:7]3[N:3]([CH2:1][CH3:2])[C:4](=[O:26])[N:5]([CH2:24][CH3:25])[C:6]=3[CH:11]=2)[CH:16]=[N:15]1)([CH3:37])([CH3:36])[CH3:35]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 516892Sodium BicarbonateHCID 178462973HCID 178462973, compound

Product 2

HCID 23581783HCID 23581783, compoundHCID 23581784HCID 23581784, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1,3-Diethyl-5-(3-m-tolyl-1H-pyrazol-4-yl)-1,3-dihydro-benzoimidazol-2-one (310 mg, 0.896 mmol) was diluted with dioxane (4 mL) and treated with sodium hydride (61.4 mg, 60% oil dispersion). After stirring at 23° C. for 0.5 hour t-butyl bromoacetate (0.25 mL) was added and the mixture was allowed to stir for 1 hour then was poured onto saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried with sodium sulfate and concentrated. Silica gel chromatography gave [4-(1,3-Diethyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-3-m-tolyl-pyrazol-1-yl]-acetic acid tert-butyl ester (0.122 g) and [4-(1,3-Diethyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-5-m-tolyl-pyrazol-1-yl]-acetic acid tert-butyl ester (0.135 g).

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9286be4b826c49f98afe06e155b72a7e
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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