Water → Ethyl{[(5-{3-[(tert-butoxycarbonyl)amino]phenoxy}pyridin-2-yl)amino]carbonothioyl}carbamate

HRID 1800398

Reaktionsgleichung

Reaktionsgleichung von HRID 1800398
[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:16]=[N:17][C:18]([NH2:21])=[CH:19][CH:20]=2)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:23]([O:25][C:26]([N:28]=[C:29]=[S:30])=[O:27])[CH3:24].O>CS(C)=O>[CH2:23]([O:25][C:26](=[O:27])[NH:28][C:29]([NH:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:22])[CH:9]=2)=[CH:16][N:17]=1)=[S:30])[CH3:24]

Komponenten

5

Edukt 3

HCID 962WaterHCID 85320Ethyl isothiocyanatoformateHCID 57749334Tert-butyl 3-(6-aminopyridin-3-yloxy)phenylcarbamate

Produkt 1

HCID 91208855Ethyl{[(5-{3-[(tert-butoxycarbonyl)amino]phenoxy}pyridin-2-yl)amino]carbonothioyl}carbamateAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl{3-[(6-aminopyridin-3-yl)oxy]phenyl}carbamate (4.60 g, 15.2 mmol) in dimethyl sulfoxide (90 mL) was added ethoxycarbonyl isothiocyanate (2.00 mL, 16.7 mmol), and the mixture was stirred at room temperature for 5 days. Water (200 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (400 mL). The organic layer was washed with 5% aqueous ammonium chloride solution (200 mL), 5% aqueous sodium hydrogen carbonate solution (200 mL) and saturated brine (200 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10→50/50), and fractions containing the object product was concentrated under reduced pressure to give the title compound (4.56 g, 69%) as a colorless solid.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate (400 mL)
  2. washThe organic layer was washed with 5% aqueous ammonium chloride solution (200 mL), 5% aqueous sodium hydrogen carbonate solution (200 mL) and saturated brine (200 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10→50/50), and fractions
  7. additioncontaining the object product
  8. concentrationwas concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a97527d43a6e4f9a881375ba4d6f516a
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344135B2

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