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

HRID 1841946
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HRID 1841946 반응식
[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
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-2a9510bf8eea48eb89d49af6327453f4
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08946197B2

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