Sodium Thiosulfate → 6,6-Dimethyl-11-oxo-8-(4-oxo-piperidin-1-yl)-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 61739
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]3[C:23](=[O:24])[C:22]4[C:21]5[C:16](=[CH:17][C:18]([C:25]#[N:26])=[CH:19][CH:20]=5)[NH:15][C:14]=4[C:13]([CH3:28])([CH3:27])[C:12]=3[CH:29]=2)[CH2:4][CH2:3]1.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+].COC1CCCC1>C(Cl)Cl.CN(C=O)C>[CH3:27][C:13]1([CH3:28])[C:14]2[NH:15][C:16]3[C:21](=[CH:20][CH:19]=[C:18]([C:25]#[N:26])[CH:17]=3)[C:22]=2[C:23](=[O:24])[C:11]2[CH:10]=[CH:9][C:8]([N:5]3[CH2:6][CH2:7][C:2](=[O:1])[CH2:3][CH2:4]3)=[CH:29][C:12]1=2

Komponenten

7

Edukt 4

HCID 24477Sodium ThiosulfateHCID 138539Cyclopentyl methyl etherHCID 516892Sodium BicarbonateHCID 545808688-(4-hydroxypiperidin-1-yl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

Produkt 1

HCID 668341076,6-Dimethyl-11-oxo-8-(4-oxo-piperidin-1-yl)-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

8-(4-Hydroxy-piperidin-1-yl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound B2-7-1, 210 mg, 0.545 mmol), was dissolved in the DCM (2 mL) and DMF (0.6 mL) mixture solvent, added with 1,1,1-triacetoxy-1,1-dihydro-1,2-benzoiodoxol-3(1H)-one (300 mg, 1.3 eq.), and the mixture was stirred at room temperature for 2 hr. To the reaction solution, 0.25 mol/L aqueous solution of sodium thiosulfate, saturated sodium bicarbonate solution and CPME were added followed by further stirring at room temperature for 1 hr. The reaction solution was filtered and the filtrate was subjected to liquid separation. The organic layer was washed with saturated 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 silica gel column chromatography (ethyl acetate/hexane) to obtain the target compound (yellowish white powder, 109 mg, 52%).

Aufarbeitung

  1. stirringby further stirring at room temperature for 1 hr
  2. filtrationThe reaction solution was filtered
  3. customthe filtrate was subjected to liquid separation
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. customThe drying agent was removed by filtration
  7. customthe residues obtained
  8. concentrationafter concentration under reduced pressure
  9. customwere purified by silica gel column chromatography (ethyl acetate/hexane)
  10. customto obtain the target compound (yellowish white powder, 109 mg, 52%)

Quellen und Nachweise

ORD-Eintrag
ord-793af4ee323a4588874b467dbc991562
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440922B2

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