Ethyl bromoacetate → HCID 19357123, compound

HRID 377913Notes

Reaction equation

HRID 377913 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[C:24]([O:30][CH3:31])[CH:23]=3)[CH2:18][CH2:17]2)=[O:15])[C:7]([O:11][CH3:12])=[N:8][C:9]=1[CH3:10])(=[O:3])[CH3:2].[H-].[Na+].[CH2:34]([O:36][C:37](=[O:40])[CH2:38]Br)[CH3:35]>>[CH3:29][O:28][C:26]1[CH:27]=[C:22]([N:19]2[CH2:20][CH2:21][N:16]([C:14]([N:13]([C:6]3[C:7]([O:11][CH3:12])=[N:8][C:9]([CH3:10])=[C:4]([C:1](=[O:3])[CH3:2])[CH:5]=3)[CH2:38][C:37]([O:36][CH2:34][CH3:35])=[O:40])=[O:15])[CH2:17][CH2:18]2)[CH:23]=[C:24]([O:30][CH3:31])[CH:25]=1

Participants

4

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 19356998HCID 19356998, compound

Product 1

HCID 19357123HCID 19357123, compoundYield 84%

Procedure

1-[(5-Acetyl-2-methoxy-6-methylpyridin-3-yl)aminocarbonyl]-4-(3,5-dimethoxylphenyl)piperazine(200 mg, 0.5 mmol) was dissolved in dimethylfornamide(15 ml) and thereto sodium hydride(18.5 mg, 0.5 mmol) was added, then followed by stirring at room temperature for 15 min, and ethylbromoacetate(83.5 mg, 0.5 mmol) was added. The resulting mixture was stirred at room temperature for 3 hrs, concentrated under the reduced pressure to remove the used solvent, and purified by column chromatography(ethylacetate:hexane=1:2) to obtain the titled compound.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 3 hrs
  2. concentrationconcentrated under the reduced pressure
  3. customto remove the used solvent
  4. custompurified by column chromatography(ethylacetate:hexane=1:2)

Sources & evidence

ORD record
ord-a3e8070cbc69429b904327e300ea44b7
Source dataset
uspto-grants-2000_02
Patent number
US06028195

Reaction notes

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