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1h-1,2,4-Triazole sodium salt → 4-[[2-(1h-1,2,4-Triazol-1-yl)ethyl](2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

HRID 1173513
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HRID 1173513 반응식
CS(O[CH2:6][CH2:7][N:8]([C:14]1[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[C:16]([C:22]([F:25])([F:24])[F:23])[CH:15]=1)[CH2:9][C:10]([F:13])([F:12])[F:11])(=O)=O.[Na].[NH:27]1[CH:31]=[N:30][CH:29]=[N:28]1>CN(C=O)C>[N:27]1([CH2:6][CH2:7][N:8]([CH2:9][C:10]([F:13])([F:12])[F:11])[C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[C:16]([C:22]([F:25])([F:24])[F:23])[CH:15]=2)[CH:31]=[N:30][CH:29]=[N:28]1
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참가 물질

4

반응물 2

HCID 454898221h-1,2,4-Triazole sodium saltHCID 866237322-[[4-Cyano-3-(trifluoromethyl)phenyl](2,2,2-trifluoroethyl)amino]ethyl methanesulfonate

생성물 1

HCID 875240344-[[2-(1h-1,2,4-Triazol-1-yl)ethyl](2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile수율 83%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

A mixture of 2-[[4-cyano-3-(trifluoromethyl)phenyl](2,2,2-trifluoroethyl)amino]ethyl methanesulfonate, Example 15C (0.050 g, 0.128 mmol) and 1,2,4-triazole sodium salt (0.023 g, 0.256 mmol) in DMF (2 mL) was heated at 60° C. under N2 for 45 min. Upon cooling, the mixture was partitioned between Et2O and water. The organic phase was washed with water and the combined aqueous phases were extracted twice with Et2O. The combined organic phases were washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by silica gel chromatography (5-80% EtOAc/hexanes gradient followed by 1-10% MeOH/EtOAc gradient) and the product was crystallized from CH2Cl2/hexanes to give the title compound as a white solid (0.038 mg, 83% yield): MS (ES) m/z 364 (M+1).

후처리

  1. temperatureUpon cooling
  2. customthe mixture was partitioned between Et2O and water
  3. washThe organic phase was washed with water
  4. extractionthe combined aqueous phases were extracted twice with Et2O
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography (5-80% EtOAc/hexanes gradient followed by 1-10% MeOH/EtOAc gradient)
  9. customthe product was crystallized from CH2Cl2/hexanes

출처 및 근거

ORD 기록
ord-1e6b7ba03a114ff3b4beaf79598b3c67
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07834063B2

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