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Piperidine → 2-[4-(1H-indol-3-ylmethylene)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-phenyl-acetamide

HRID 900110
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 900110
[CH:1]([N:4]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:5](=[O:28])[CH2:6][N:7]1[C:16](=[O:17])[CH2:15][C:14]2[N:10]([C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:12][N:13]=2)[C:9]2[CH:24]=[CH:25][CH:26]=[CH:27][C:8]1=2)([CH3:3])[CH3:2].[NH:35]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:37]([CH:44]=O)=[CH:36]1.N1CCCCC1>C1(C)C=CC=CC=1>[NH:35]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:37]([CH:44]=[C:15]2[C:14]3[N:10]([C:11]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[N:12][N:13]=3)[C:9]3[CH:24]=[CH:25][CH:26]=[CH:27][C:8]=3[N:7]([CH2:6][C:5]([N:4]([CH:1]([CH3:3])[CH3:2])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:28])[C:16]2=[O:17])=[CH:36]1
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Komponenten

5

Edukt 3

HCID 8082PiperidineHCID 10256Indole-3-CarboxaldehydeHCID 58957944N-isopropyl-2-(5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-N-phenyl-acetamide

Produkt 1

HCID 1363524502-[4-(1H-indol-3-ylmethylene)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-phenyl-acetamideAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of N-isopropyl-2-(5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-N-phenyl-acetamide (Preparation 7(A)) (1.2 g, 2.7 mmol) in toluene (15 mL) was added 1H-indole-3-carbaldehyde (0.46 g, 3.2 mmol) and piperidine (0.4 mL). The reaction mixture was heated to reflux for 14 hours. Activated 4 Å molecular sieves (2 g) were added and the reaction mixture was refluxed for 24 hours. The sieves were removed by filtration and the filtrate was concentrated. The residue was triturated with methylene chloride and the solid was collected via filtration and was dried in vacuo to give 1.5 g of 2-[4-(1H-indol-3-ylmethylene)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-phenyl-acetamide. The filtrate was concentrated and was purified by chromatography (20% acetone/methylene chloride) to afford an additional 320 mg of 2-[4-(1H-indol-3-ylmethylene)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-phenyl-acetamide. MS 579.2 (M+1).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 14 hours
  3. additionActivated 4 Å molecular sieves (2 g) were added
  4. temperaturethe reaction mixture was refluxed for 24 hours
  5. customThe sieves were removed by filtration
  6. concentrationthe filtrate was concentrated
  7. customThe residue was triturated with methylene chloride
  8. filtrationthe solid was collected via filtration
  9. customwas dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5a3fbd50327a4859a3e221bd9903799c
Quelldatensatz
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07358242B2

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