HOAt → (E)-2-Chloro-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)-N-(1-(2,2,2-trifluoroethylcarbamoyl)cyclopropyl)benzamide

HRID 1503784노트

반응식

HRID 1503784 반응식
[Cl:1][C:2]1[CH:10]=[C:9](/[CH:11]=[CH:12]/[CH:13]([C:18]2[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[C:20]([Cl:26])[CH:19]=2)[C:14]([F:17])([F:16])[F:15])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:27][C:28]1([C:31]([NH:33][CH2:34][C:35]([F:38])([F:37])[F:36])=[O:32])[CH2:30][CH2:29]1.F[P-](F)(F)(F)(F)F.ClC1N(C)CC[NH+]1C.ON1C2N=CC=CC=2N=N1>C(Cl)Cl.CN(C=O)C.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:10]=[C:9](/[CH:11]=[CH:12]/[CH:13]([C:18]2[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[C:20]([Cl:26])[CH:19]=2)[C:14]([F:16])([F:15])[F:17])[CH:8]=[CH:7][C:3]=1[C:4]([NH:27][C:28]1([C:31](=[O:32])[NH:33][CH2:34][C:35]([F:37])([F:38])[F:36])[CH2:30][CH2:29]1)=[O:6]

참가 물질

7

반응물 4

HCID 181649HOAtHCID 218684192-Chloro-1,3-dimethylimidazolidin-1-ium;hexafluorophosphateHCID 654644011-amino-N-(2,2,2-trifluoroethyl)cyclopropanecarboxamideHCID 86722568(E)-2-chloro-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)benzoic acid

생성물 1

HCID 86722567(E)-2-Chloro-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)-N-(1-(2,2,2-trifluoroethylcarbamoyl)cyclopropyl)benzamide수율 75%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 22350042dichloromethane N,N-dimethylformamide용매

실험 절차

To a stirred solution of (E)-2-chloro-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)benzoic acid (300 mg, 0.67 mmol) and 1-amino-N-(2,2,2-trifluoroethyl)cyclopropanecarboxamide (148 mg, 0.81 mmol) in DCM/DMF (5 mL, 1:1), 2-chloro-1,3-dimethylimidazolidinium hexafluorophosphate (CIP) (92 mg, 0.33 mmol), 1-hydroxy-7-azabenzotriazole (HOAt) (48 mg, 0.33 mmol) and DMAP (5 mol %) were added, and the resulting mixture was stirred at room temperature (RT) for 4 h. The reaction mixture was poured into ice-water and extracted with EtOAc. The organic phase was dried (Na2SO4), filtered, concentrated and the residue was purified by column chromatography on silica (100-200 mesh) eluting with 30% EtOAc in petroleum ether to give the title compound as pale yellow gum (300 mg, 75%). Characterization data for this molecule is listed in Table 2.

후처리

  1. extractionextracted with EtOAc
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified by column chromatography on silica (100-200 mesh)
  6. washeluting with 30% EtOAc in petroleum ether

출처 및 근거

ORD 기록
ord-1d76034e53a8425d884b4ca8f3e8a555
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212164B2

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