Acryloyl chloride → 4-(4-Acryloylamino-2-trifluoromethyl-benzenesulfonyl)-piperazine-1-carboxylic acid benzyl ester

HRID 1841946Notes

Reaction equation

HRID 1841946 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][C:21]=2[C:27]([F:30])([F:29])[F:28])(=[O:19])=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[C:40](Cl)(=[O:43])[CH:41]=[CH2:42]>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:40](=[O:43])[CH:41]=[CH2:42])=[CH:22][C:21]=2[C:27]([F:30])([F:28])[F:29])(=[O:19])=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 569549454-(4-Amino-2-trifluoromethyl-benzenesulfonyl)-piperazine-1-carboxylic acid benzyl ester

Product 1

HCID 529397714-(4-Acryloylamino-2-trifluoromethyl-benzenesulfonyl)-piperazine-1-carboxylic acid benzyl esterYield 127.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(4-Amino-2-trifluoromethyl-benzensulfonyl)-piperazine-1-carboxylic acid benzyl ester (0.44 g, 0.11 mmol) was dissolved in THF (15 ml). To this solution was added diisopropylethylamine (0.52 ml, 0.33 mmol) in one portion followed by the drop wise addition of acryloyl chloride (0.09 ml, 0.11 mmol) and the mixture was stirred at room temperature under a nitrogen atmosphere for 3 hours. The THF was removed under vacuum and the resulting crude material, was purified by preparative HPLC to give the title compound (70 mg, 14% yield) as a white solid.

Workup

  1. customThe THF was removed under vacuum
  2. customthe resulting crude material, was purified by preparative HPLC

Sources & evidence

ORD record
ord-2a9510bf8eea48eb89d49af6327453f4
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Reaction notes

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