4,4,4-Trifluoro-1-(3-chloro-4-methoxylphenyl)-1,3-butanedione → 2-[5-(3-Chloro-4-methoxy-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-5-methanesulfonyl-pyridine

HRID 1860584노트

반응식

HRID 1860584 반응식
[F:1][C:2]([F:18])([F:17])[C:3](=O)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([Cl:15])[CH:8]=1)=O.Cl.[NH:20]([C:22]1[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][N:23]=1)[NH2:21]>C(O)C>[CH2:22]([NH:23][CH2:24][CH3:25])[CH3:27].[Cl:15][C:9]1[CH:8]=[C:7]([C:5]2[N:20]([C:22]3[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][N:23]=3)[N:21]=[C:3]([C:2]([F:18])([F:17])[F:1])[CH:4]=2)[CH:12]=[CH:11][C:10]=1[O:13][CH3:14]

참가 물질

5

반응물 2

HCID 129727284,4,4-Trifluoro-1-(3-chloro-4-methoxylphenyl)-1,3-butanedioneHCID 222268132-Hydrazino-5-(methylsulfonyl)pyridine hydrochloride

생성물 2

HCID 8021DiethylamineHCID 101376372-[5-(3-Chloro-4-methoxy-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-5-methanesulfonyl-pyridine수율 59.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

4,4,4-Trifluoro-1-(3-chloro-4-methoxylphenyl)-1,3-butanedione (1.2 g, 4.29 mmol) and 2-hydrazino-5-(methylsulfonyl)pyridine hydrochloride (1.00 g, 4.46 mmol) were mixed in ethanol (60 ml), and the resulting reaction mixture was heated at reflux temperature overnight. The reaction mixture was then cooled to room temperature, and the solvent was removed in vacuo. The residue was dissolved in EtOAc (250 ml), and the organic layer was washed with saturated NaHCO3 solution, brine, dried (MgSO4), and concentrated in vacuo. The residue was purified by flash chromatography first using 7:3:1 of hexane:diethylamine:methanol and then 20% hexane in methylene chloride to give the title compound (570 mg, 31%).

후처리

  1. customthe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux temperature overnight
  4. customthe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in EtOAc (250 ml)
  6. washthe organic layer was washed with saturated NaHCO3 solution, brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-e64f0ae7fc6a45d288ebd7cb4b721e46
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06531492B1

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