Tert-Butylamine → 8-(2-Tert-butylamino-ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 2202450

Reaktionsgleichung

Reaktionsgleichung von HRID 2202450
OC1C=CC2C(=O)C3C4C(=CC(C#N)=CC=4)NC=3C(C)(C)C=2C=1.ClCCN(CC)CC.C(=O)([O-])[O-].[Cs+].[Cs+].C(N(CC)[CH2:41][CH2:42][O:43][C:44]1[CH:45]=[CH:46][C:47]2[C:59](=[O:60])[C:58]3[C:57]4[C:52](=[CH:53][C:54]([C:61]#[N:62])=[CH:55][CH:56]=4)[NH:51][C:50]=3[C:49]([CH3:64])([CH3:63])[C:48]=2[CH:65]=1)C.[C:68]([NH2:72])([CH3:71])([CH3:70])[CH3:69]>CN(C)C(=O)C.O>[C:68]([NH:72][CH2:41][CH2:42][O:43][C:44]1[CH:45]=[CH:46][C:47]2[C:59](=[O:60])[C:58]3[C:57]4[C:52](=[CH:53][C:54]([C:61]#[N:62])=[CH:55][CH:56]=4)[NH:51][C:50]=3[C:49]([CH3:64])([CH3:63])[C:48]=2[CH:65]=1)([CH3:71])([CH3:70])[CH3:69]

Komponenten

8

Edukt 5

HCID 6385Tert-ButylamineHCID 10796Cesium carbonateHCID 13364Diethylaminoethyl chlorideHCID 545808678-(2-(diethylamino)ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileHCID 668338618-Hydroxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile2×

Produkt 1

HCID 498048718-(2-Tert-butylamino-ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

With the same synthesis condition as the Compound A7-17 (8-hydroxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound A6, 25 mg, 0.083 mmol) was dissolved in N,N-dimethylacetamide (1 mL), added with 2-chloroethyldiethylamine (16 mg, 1.1 eq.) and cesium carbonate (54 mg, 2 eq.) in order and stirred at 100° C. for 4 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium 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 (ethyl acetate/hexane) to obtain the Compound A7-17 (8-(2-diethylamino-ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile) (11 mg, 32%)), the title compound was synthesized from the Compound A7-24 and tert-butyl amine.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe drying agent was removed by filtration
  5. customthe residues obtained
  6. concentrationafter concentration under reduced pressure
  7. customwere purified by amino silica gel column chromatography (ethyl acetate/hexane)
  8. customto obtain the Compound

Quellen und Nachweise

ORD-Eintrag
ord-9438962a4ed14eb4ae69476d666df3cb
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365514B2

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