Stannous chloride dihydrate → 5-amino-N,N-diethyl-6-(2-propenylamino)-3-pyridinecarboxamide

HRID 1796519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1796519
[CH2:1]([N:3]([CH2:19][CH3:20])[C:4]([C:6]1[CH:7]=[N:8][C:9]([NH:15][CH2:16][CH:17]=[CH2:18])=[C:10]([N+:12]([O-])=O)[CH:11]=1)=[O:5])[CH3:2].O.O.[Sn](Cl)Cl>CN(C=O)C>[NH2:12][C:10]1[CH:11]=[C:6]([C:4]([N:3]([CH2:19][CH3:20])[CH2:1][CH3:2])=[O:5])[CH:7]=[N:8][C:9]=1[NH:15][CH2:16][CH:17]=[CH2:18]

Komponenten

4

Edukt 2

HCID 61436Stannous chloride dihydrateHCID 22181420N,N-diethyl-5-nitro-6-(2-propenylamino)-3-pyridinecarboxamide

Produkt 1

HCID 221813075-amino-N,N-diethyl-6-(2-propenylamino)-3-pyridinecarboxamideAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of N,N-diethyl-5-nitro-6-(2-propenylamino)-3-pyridinecarboxamide (4.83 g, 17.25 mmol) in DMF (50 mL) at room temperature was added tin dichloride dihydrate (8.56 g, 37.95 mmol). The mixture was stirred overnight at 80° C. The reaction was brought to room temperature and concentrated in vacuo. The residue was taken up into NaHCO3 saturated aqueous solution (100 mL) and EtOAc (100 mL). The suspension was filtered and the phases separated. The aqueous phase was back-extracted with additional EtOAc (100 mL). The organic phases were combined, dried with MgSO4, filtered and concentrated in vacuo. The residue was purified using silica gel flash chromatography ([5% MeOH+1% NH4OH aq] in CH2Cl2) to provide 2.10 g of the title compound 5-amino-N,N-diethyl-6-(2-propenylamino)-3-pyridinecarboxamide (49.0% yield from N,N-diethyl-5-nitro-6-(2-propenylamino)-3-pyridinecarboxamide). 1H-NMR (400 MHz, CDCl3): δ 1.20 (t, J=7.2 Hz, 6H), 3.23 (br s, 1H), 3.45 (m,4H), 4.12 (m, 2H), 4.44 (br s, 2H), 5.17 (d, J=12.5 Hz, 1H), 5.26 (d, J=17.2 Hz, 1H), 6.04 (m, 1H), 7.00 (d, J=2.0 Hz, 1H), 7.83 (d, J=2.0 Hz, 1H). MS (ESI) (M+H)+: 2.49.

Aufarbeitung

  1. customwas brought to room temperature
  2. concentrationconcentrated in vacuo
  3. filtrationThe suspension was filtered
  4. customthe phases separated
  5. extractionThe aqueous phase was back-extracted with additional EtOAc (100 mL)
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-5c31a14d25954c05a07392308f95fe56
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07030139B2

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