1-Hydroxybenzotriazole → HCID 178477270、化合物

HRID 533641ノート

反応式

HRID 533641 の反応式
[F:1][C:2]([C:11]1[CH:12]=[C:13]([NH2:18])[C:14]([NH2:17])=[CH:15][CH:16]=1)([C:7]([F:10])([F:9])[F:8])[C:3]([F:6])([F:5])[F:4].[CH2:19]([S:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](O)=O)[CH3:20].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>O.N1C=CC=CC=1>[CH2:19]([S:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24]1[NH:17][C:14]2[CH:15]=[CH:16][C:11]([C:2]([F:1])([C:7]([F:8])([F:9])[F:10])[C:3]([F:6])([F:5])[F:4])=[CH:12][C:13]=2[N:18]=1)[CH3:20]

参加物

7

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 4257582-(Ethylsulfanyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 100390994-(1,2,2,2-Tetrafluoro-1-trifluoromethyl-ethyl)-benzene-1,2-diamine

生成物 1

HCID 178477270HCID 178477270、化合物収率 11.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1049Pyridine溶媒

実験手順

To a mixture of 4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-benzene-1,2-diamine (552 mg), 2-ethylsulfanylbenzoic acid (401 mg), and pyridine (27 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (422 mg) and 1-hydroxybenzotriazole (27 mg) were added at room temperature. The reaction mixture was stirred at room temperature for 5 hours, diluted with water, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was dissolved in a mixed solution of DMF (7.5 mL) and toluene (30 mL), and then p-toluenesulfonic acid (837 mg) was added at room temperature. The mixture was stirred with heating at 130° C. for 8 hours, and allowed to stand to cool to room temperature. Into the reaction mixture, saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 97 mg of 2-(2-ethylsulfanyl-phenyl)-5-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-1H-benzimidazole (hereinafter, Present Compound 346).

後処理

  1. additionwere added at room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe resulting residue was dissolved in a mixed solution of DMF (7.5 mL) and toluene (30 mL)
  6. additionp-toluenesulfonic acid (837 mg) was added at room temperature
  7. stirringThe mixture was stirred
  8. temperaturewith heating at 130° C. for 8 hours
  9. temperatureto cool to room temperature
  10. additionInto the reaction mixture, saturated aqueous sodium hydrogen carbonate solution was poured
  11. extractionextracted with ethyl acetate
  12. dry with materialThe combined organic layer was dried over sodium sulfate
  13. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-5139a3cc94df4984a9836553fd3016c2
出典データセット
uspto-grants-2014_10
特許番号
US08853238B2

反応ノート

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