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Diisopropylethylamine → 6,6-Dimethyl-11-oxo-8-[2-(3-oxo-piperazin-1-yl)-ethoxy]-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 2275095
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2275095
Br[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[C:20](=[O:21])[C:19]3[C:18]4[C:13](=[CH:14][C:15]([C:22]#[N:23])=[CH:16][CH:17]=4)[NH:12][C:11]=3[C:10]([CH3:25])([CH3:24])[C:9]=2[CH:26]=1.[NH:27]1[CH2:32][CH2:31][NH:30][CH2:29][C:28]1=[O:33].C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:25][C:10]1([CH3:24])[C:11]2[NH:12][C:13]3[C:18](=[CH:17][CH:16]=[C:15]([C:22]#[N:23])[CH:14]=3)[C:19]=2[C:20](=[O:21])[C:8]2[CH:7]=[CH:6][C:5]([O:4][CH2:3][CH2:2][N:30]3[CH2:31][CH2:32][NH:27][C:28](=[O:33])[CH2:29]3)=[CH:26][C:9]1=2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 231360Piperazin-2-oneHCID 66833930HCID 66833930, Verbindung

Produkt 1

HCID 668340626,6-Dimethyl-11-oxo-8-[2-(3-oxo-piperazin-1-yl)-ethoxy]-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To DMF solution (5 mL) of 8-(2-bromo-ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound A7-24, 30 mg, 0.07 mmol), piperazin-2-one (44.9 mg, 0.35 mmol) and N,N-diisopropylethylamine (0.061 mL, 0.35 mmol) were added at room temperature and stirred at 80° C. for 18 hr. After cooling to room temperature, the mixture was extracted with ethyl acetate washed with saturated brine. 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 preparative TLC (dichloromethane/methanol) to obtain the title compound (white solid, 24 mg, 80%).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customThe drying agent was removed by filtration
  6. customthe residues obtained
  7. concentrationafter concentration under reduced pressure
  8. customwere purified by preparative TLC (dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-233292df729344f59e7b2141ceb07867
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09126931B2

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