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

HRID 900084

Reaktionsgleichung

Reaktionsgleichung von HRID 900084
[CH:1]([N:4]([C:29]1[CH:30]=[N:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=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].[F:37][C:38]1[CH:46]=[C:45]2[C:41]([C:42]([CH:47]=O)=[CH:43][NH:44]2)=[CH:40][CH:39]=1.N1CCCCC1>C1(C)C=CC=CC=1.O>[F:37][C:38]1[CH:46]=[C:45]2[C:41]([C:42]([CH:47]=[C:15]3[C:14]4[N:10]([C:11]([C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=5)=[N:12][N:13]=4)[C:9]4[CH:24]=[CH:25][CH:26]=[CH:27][C:8]=4[N:7]([CH2:6][C:5]([N:4]([CH:1]([CH3:3])[CH3:2])[C:29]4[CH:30]=[N:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=4)=[O:28])[C:16]3=[O:17])=[CH:43][NH:44]2)=[CH:40][CH:39]=1

Komponenten

6

Edukt 3

HCID 8082PiperidineHCID 2629036-Fluoroindole-3-carboxaldehydeHCID 58957931N-isopropyl-N-(6-methoxy-pyridin-3-yl)-2-(5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-acetamide

Produkt 1

HCID 1363477452-[4-(6-fluoro-1H-indol-3-ylmethylene)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-(6-methoxy-pyridin-3-yl)-acetamideAusbeute 80,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

To a solution of N-isopropyl-N-(6-methoxy-pyridin-3-yl)-2-(5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-acetamide (Preparation 11) (150 mg, 0.311 mmol) and 6-fluoro-1H-indole-3-carbaldehyde (61 mg, 0.373 mmol) in toluene (20 mL) was added piperidine (100 μL). The reaction vessel was equipped with a Dean-Stark trap that contained toluene and 4A molecular sieves and was heated at reflux for 24 hours. The solution was cooled to room temperature and was diluted with water. The aqueous solution was washed with EtOAc (3×) and the combined organic extracts were dried (MgSO4), filtered and concentrated. The residue was purified by medium pressure chromatography eluting with a solvent gradient (10% EtOAc in hexanes to 100% EtOAc) to yield 158 mg of 2-[4-(6-fluoro-1H-indol-3-ylmethylene)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-(6-methoxy-pyridin-3-yl)-acetamide. MS 628.3 (M+1), 626.2 (M−1).

Aufarbeitung

  1. customThe reaction vessel was equipped with a Dean-Stark trap that
  2. temperaturewas heated
  3. temperatureat reflux for 24 hours
  4. washThe aqueous solution was washed with EtOAc (3×)
  5. dry with materialthe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by medium pressure chromatography
  9. washeluting with a solvent gradient (10% EtOAc in hexanes to 100% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-08cf75bfd79c4054b484f424eba62193
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07358242B2

Verknüpfte Notizen

Wird geladen…