Methyl iodide → 4-[4-(Acryloyl-methyl-amino)-benzenesulfonyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 1841925Notes

Reaction equation

HRID 1841925 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([S:16]([C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:29])[CH:27]=[CH2:28])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:30]I>C1COCC1>[C:3]([O:7][C:8]([N:10]1[CH2:11][CH2:12][N:13]([S:16]([C:19]2[CH:20]=[CH:21][C:22]([N:25]([C:26](=[O:29])[CH:27]=[CH2:28])[CH3:30])=[CH:23][CH:24]=2)(=[O:17])=[O:18])[CH2:14][CH2:15]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 529395194-(4-Acryloylamino-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 569537314-[4-(Acryloyl-methyl-amino)-benzenesulfonyl]-piperazine-1-carboxylic acid tert-butyl esterYield 7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (0.050 g, 26 mmol) was added in one portion to a stirred solution of 4-(4-acryloylamino-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester (0.1 g, 0.25 mmol) in THF (1 ml). The reaction was stirred at room temperature for 5 minutes before methyl iodide (0.05 g, 0.25 mmol) was added in one portion and stirring continued for 1 hour. After this time, the reaction mixture was concentrated under vacuum and the resulting residue purified by prep HPLC to give the title compound (6.6 mg, 7% yield) as a white solid.

Workup

  1. additionwas added in one portion
  2. concentrationAfter this time, the reaction mixture was concentrated under vacuum
  3. customthe resulting residue purified by prep HPLC

Sources & evidence

ORD record
ord-61f03b82b9ee4000b2828d5b0f441ad1
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Reaction notes

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