Water → ethyl (Z)-2-ethoxy-3-{4-[6-(1-methyl-3-pentylureido)pyrid-2-yl]phenyl}acrylate

HRID 390591Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 390591
[CH2:1]([NH2:6])[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:7]([O:9]/[C:10](=[CH:16]\[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N:29]([CH3:42])[C:30]([O:32]C3C=CC([N+]([O-])=O)=CC=3)=O)[N:24]=2)=[CH:19][CH:18]=1)/[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:8].O.C(OCC)(=O)C>CN(C)C=O>[CH2:7]([O:9]/[C:10](=[CH:16]\[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N:29]([CH3:42])[C:30]([NH:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[O:32])[N:24]=2)=[CH:19][CH:18]=1)/[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:8]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8060PentylamineHCID 8857Ethyl AcetateHCID 86626074ethyl (Z)-2-ethoxy-3-(4-{6-[methyl-(4-nitrophenoxycarbonyl)amino]pyrid-2-yl}phenyl)acrylate

Produkt 1

HCID 16224919ethyl (Z)-2-ethoxy-3-{4-[6-(1-methyl-3-pentylureido)pyrid-2-yl]phenyl}acrylateAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

0.21 mL (1.8 mmol) of n-pentylamine is added to a solution of 0.45 g (0.9 mmol) of ethyl (Z)-2-ethoxy-3-(4-{6-[methyl-(4-nitrophenoxycarbonyl)amino]pyrid-2-yl}phenyl)acrylate (prepared according to Example 2d) in 15 mL of dimethylformamide. The tube is sealed and rapidly placed in an oil bath preheated to 80° C. The reaction mixture is stirred at 80° C. for 1 hour 30 minutes. After cooling, the reaction is worked up by addition of 10 mL of water and extraction with ethyl acetate. The organic phases are combined, washed with saturated aqueous sodium chloride solution and then dried over magnesium sulfate. The solvents are evaporated off. The crude product obtained is purified by chromatography on a column of silica eluted with a 70/30 heptane/ethyl acetate mixture to give 0.2 g (57%) of ethyl (Z)-2-ethoxy-3-{4-[6-(1-methyl-3-pentylureido)pyrid-2-yl]phenyl}acrylate in the form of a pale yellow solid.

Aufarbeitung

  1. customThe tube is sealed
  2. customrapidly placed in an oil bath
  3. custompreheated to 80° C
  4. temperatureAfter cooling
  5. washwashed with saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customThe solvents are evaporated off
  8. customThe crude product obtained
  9. customis purified by chromatography on a column of silica
  10. washeluted with a 70/30 heptane/ethyl acetate mixture

Quellen und Nachweise

ORD-Eintrag
ord-10071d4b9105403faff65877a0b6e418
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383652B2

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