Water → 8-{2-(Tert-butyloxycarbonylaminosulfonyl)amino-ethoxy}-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 2275098Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2275098
FC(F)(F)C(O)=O.[NH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[C:27](=[O:28])[C:26]3[C:25]4[C:20](=[CH:21][C:22]([C:29]#[N:30])=[CH:23][CH:24]=4)[NH:19][C:18]=3[C:17]([CH3:32])([CH3:31])[C:16]=2[CH:33]=1.[C:34]([O:38][C:39]([N-:41][S:42](N1C=CC(=[N+](C)C)C=C1)(=[O:44])=[O:43])=[O:40])([CH3:37])([CH3:36])[CH3:35].O>N1C=CC=CC=1>[C:34]([O:38][C:39]([NH:41][S:42]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[C:27](=[O:28])[C:26]3[C:25]4[C:20](=[CH:21][C:22]([C:29]#[N:30])=[CH:23][CH:24]=4)[NH:19][C:18]=3[C:17]([CH3:31])([CH3:32])[C:16]=2[CH:33]=1)(=[O:44])=[O:43])=[O:40])([CH3:37])([CH3:35])[CH3:36]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 668337928-(2-amino-ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileHCID 178482962HCID 178482962, Verbindung

Produkt 1

HCID 668341498-{2-(Tert-butyloxycarbonylaminosulfonyl)amino-ethoxy}-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileAusbeute 69,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid salt of 8-(2-amino-ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound A8-2, 20 mg, 0.044 mmol) was dissolved in pyridine (0.5 mL), added with N-(tert-butoxycarbonyl)-N-[4-(dimethyl azaniumylidene)-1,4-dihydropyridin-1-yl sulfonyl]azanide (13.5 mg, 1 eq.), and then stirred at room temperature for 14 hr. The reaction solution was added to water, and then extracted with ethyl acetate. After washing with saturated brine, the organic layer was dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were separated by silica gel preparative TLC (ethyl acetate) to obtain the title compound (16.1 mg, 68%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washAfter washing with saturated brine
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. customThe drying agent was removed by filtration
  5. customthe residues obtained
  6. concentrationafter concentration under reduced pressure
  7. customwere separated by silica gel preparative TLC (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-fdf5796fbc3645ebaba2abe119b10398
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09126931B2

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