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 1860584

反応式

HRID 1860584 の反応式
[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]

参加物

5

反応物 2

HCID 129727284,4,4-Trifluoro-1-(3-chloro-4-methoxylphenyl)-1,3-butanedioneHCID 22226813HCID 22226813、化合物

生成物 2

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-e64f0ae7fc6a45d288ebd7cb4b721e46
出典データセット
uspto-grants-2003_03
特許番号
US06531492B1

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