Cyclopropanecarbonyl chloride → N-[6-(3-nitrophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

HRID 1874399

Reaktionsgleichung

Reaktionsgleichung von HRID 1874399
[N+:1]([C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][CH:20]=1)[O:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([CH:14]=[C:15]([NH2:17])[N:16]=2)[CH:13]=1)([O-:3])=[O:2].[CH:21]1([C:24](Cl)=[O:25])[CH2:23][CH2:22]1>N1C=CC=CC=1.O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][CH:20]=1)[O:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([CH:14]=[C:15]([NH:17][C:24]([CH:21]3[CH2:23][CH2:22]3)=[O:25])[N:16]=2)[CH:13]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 577492806-(3-Nitrophenoxy)imidazo[1,2-a]pyridin-2-amine

Produkt 1

HCID 57749101N-[6-(3-nitrophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamideAusbeute 35,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of 6-(3-nitrophenoxy)imidazo[1,2-a]pyridin-2-amine (1.40 g, 5.18 mmol) in pyridine (6 mL) was added with stirring under ice-cooling cyclopropanecarbonyl chloride (706 μL, 7.77 mmol), and the mixture was stirred at room temperature for 3 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was dissolved in methanol (50 mL). Sodium carbonate (1.00 g) and water (5 mL) were added, and the mixture was stirred at 60° C. for 2 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate) to give the title compound (622 mg, 35%) as a white solid.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 3 hr
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltrated
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. dissolutionthe residue was dissolved in methanol (50 mL)
  8. additionSodium carbonate (1.00 g) and water (5 mL) were added
  9. stirringthe mixture was stirred at 60° C. for 2 hr
  10. additionThe reaction mixture was diluted with water
  11. extractionextracted with ethyl acetate
  12. washThe organic layer was washed with water and saturated brine
  13. dry with materialdried over anhydrous magnesium sulfate
  14. filtrationfiltrated
  15. concentrationThe filtrate was concentrated under reduced pressure
  16. customthe residue was purified by column chromatography (silica gel, ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-52760e24bd6040f2b30d003fed947550
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304557B2

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