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Tetrahydrofuran → 9-Acetyl-8-[4-(1,1-dimethyl-prop-2-ynyl)-piperazin-1-yl]-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61796
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 61796
C1COCC1.[C:6]([C:9]1[C:30]([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:29][C:12]2[C:13]([CH3:28])([CH3:27])[C:14]3[NH:15][C:16]4[C:21]([C:22]=3[C:23](=[O:24])[C:11]=2[CH:10]=1)=[CH:20][CH:19]=[C:18]([C:25]#[N:26])[CH:17]=4)(=[O:8])[CH3:7].Cl[C:38]([CH3:42])([CH3:41])[C:39]#[CH:40].C(N(CC)CC)C>[Cu]Cl.O>[C:6]([C:9]1[C:30]([N:31]2[CH2:32][CH2:33][N:34]([C:38]([CH3:42])([CH3:41])[C:39]#[CH:40])[CH2:35][CH2:36]2)=[CH:29][C:12]2[C:13]([CH3:28])([CH3:27])[C:14]3[NH:15][C:16]4[C:21]([C:22]=3[C:23](=[O:24])[C:11]=2[CH:10]=1)=[CH:20][CH:19]=[C:18]([C:25]#[N:26])[CH:17]=4)(=[O:8])[CH3:7]
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Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 706791-Butyne, 3-chloro-3-methyl-HCID 668342259-acetyl-6,6-dimethyl-11-oxo-8-piperazin-1-yl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

Produkt 1

HCID 866638229-Acetyl-8-[4-(1,1-dimethyl-prop-2-ynyl)-piperazin-1-yl]-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile
Ausbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 62652Cuprous chlorideKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

To the anhydrous THF solution (0.5 mL) of 9-acetyl-6,6-dimethyl-11-oxo-8-piperazin-1-yl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound H8-5, 25 mg, 0.06 mmol), 3-chloro-3-methyl-but-1-yne (0.013 mL, 0.12 mmol), copper (I) chloride (0.6 mg, 0.006 mmol) and triethylamine (0.017 mL, 0.12 mmol) were added at room temperature. After stirring for 30 min, the mixture was added with water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by amino silica gel column chromatography (dichloromethane/methanol) to obtain the title compound (white solid, 9.8 mg, 35%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customThe drying agent was removed by filtration
  4. customthe residues obtained
  5. concentrationafter concentration under reduced pressure
  6. customwere purified by amino silica gel column chromatography (dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-bd5b2995ffff48a3b42d46972faac34f
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09440922B2

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