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Diisopropylethylamine → tert-butyl 4-{[5-cyano-2-(3,5-dichlorophenoxy) phenyl]sulfonyl}-3-(1H-1,2,4-triazol-1-ylmethyl)-1-piperazinecarboxylate

HRID 2242817
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HRID 2242817 반응식
[N:1]1([CH2:6][CH:7]2[NH:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]2)[CH:5]=[N:4][CH:3]=[N:2]1.C(N(C(C)C)CC)(C)C.[C:29]([C:31]1[CH:32]=[CH:33][C:34]([O:41][C:42]2[CH:47]=[C:46]([Cl:48])[CH:45]=[C:44]([Cl:49])[CH:43]=2)=[C:35]([S:37](Cl)(=[O:39])=[O:38])[CH:36]=1)#[N:30]>C1COCC1>[C:29]([C:31]1[CH:32]=[CH:33][C:34]([O:41][C:42]2[CH:47]=[C:46]([Cl:48])[CH:45]=[C:44]([Cl:49])[CH:43]=2)=[C:35]([S:37]([N:12]2[CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][CH:7]2[CH2:6][N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)(=[O:38])=[O:39])[CH:36]=1)#[N:30]
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참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 592082825-Cyano-2-(3,5-dichlorophenoxy)phenylsulfonylchlorideHCID 59208292tert-butyl 3-(1H-1,2,4-triazol-1-ylmethyl)-1-piperazinecarboxylate

생성물 1

HCID 59208297tert-butyl 4-{[5-cyano-2-(3,5-dichlorophenoxy) phenyl]sulfonyl}-3-(1H-1,2,4-triazol-1-ylmethyl)-1-piperazinecarboxylate수율 65.1%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
50 °C

실험 절차

To a solution of tert-butyl 3-(1H-1,2,4-triazol-1-ylmethyl)-1-piperazinecarboxylate (29.5 mg, 0.11 mmol) and di-isopropyl-ethyl amine (28.5 mg, 0.22 mmol) in THF (2 ml) was added 5-cyano-2-(3,5-dichlorophenoxy)benzenesulfonyl chloride (40.0 mg, 0.11 mmol). The mixture was stirred at 50° C. overnight. The solvent was removed and the residue was diluted with CHCl3, washed with sat. NaHCO3 aq. and brine. The organic layer was dried over MgSO4. The solvent was evaporated in vacuo, and the resulting residue was purified by prep. TLC (MeOH/CHCl3= 1/10) to give tert-butyl 4-{[5-cyano-2-(3,5-dichlorophenoxy)phenyl]sulfonyl}-3-(1H-1,2,4-triazol-1-yl methyl)-1-piperazine-carboxylate (42.5 mg, 64.9%): HPLC-MS (ESI): Calcd for C25H26Cl2N6O5S [M+H]+ 593, found: 593.

후처리

  1. customThe solvent was removed
  2. additionthe residue was diluted with CHCl3
  3. washwashed with sat. NaHCO3 aq. and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. customThe solvent was evaporated in vacuo
  6. customthe resulting residue was purified by prep

출처 및 근거

ORD 기록
ord-204ebf98686647b6896ebdb791ccf257
출처 데이터셋
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07674797B2

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