Water → N-(6-chloroimidazo[1,2-b]pyridazine-2-carbonyl)-2,2-dimethylglycine ethyl ester

HRID 1067596

Reaktionsgleichung

Reaktionsgleichung von HRID 1067596
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([OH:13])=O)[N:10]=2)[N:7]=1.Cl.[CH2:15]([O:17][C:18](=[O:23])[C:19]([NH2:22])([CH3:21])[CH3:20])[CH3:16].C(N(CC)CC)C.O>CN(C)C=O>[CH2:15]([O:17][C:18](=[O:23])[C:19]([CH3:21])([CH3:20])[NH:22][C:11]([C:9]1[N:10]=[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[N:7][N:6]2[CH:8]=1)=[O:13])[CH3:16]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 27946376-Chloroimidazo[1,2-b]pyridazine-2-carboxylic acidHCID 22343822Ethyl 2-amino-2-methylpropanoate hydrochloride

Produkt 1

HCID 22989357N-(6-chloroimidazo[1,2-b]pyridazine-2-carbonyl)-2,2-dimethylglycine ethyl esterAusbeute 59,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1.28 g of 6-chloroimidazo[1,2-b]pyridazine-2-carboxylic acid was suspended in 12 ml of N,N-dimethylformamide; 1.16 g of N,N′-carbonyldiimidazole was added, followed by stirring at room temperature for 30 minutes. To the reaction mixture, 1.20 g of 2-aminoisobutyric acid ethyl ester hydrochloride and 1.00 ml of triethylamine were added, followed by stirring at room temperature for 16 hours. Water was added, the crystal precipitated was collected by filtration; the filtrate was extracted with ethyl acetate; the extract was washed with saturated saline and dried with magnesium sulfate. The dry product was concentrated under reduced pressure; the residue was combined with the above crystal collected by filtration and subjected to silica gel column chromatography and eluted with hexane:ethyl acetate (2:1). The desired fraction was collected and concentrated under reduced pressure to yield 1.20 g of the title compound.

Aufarbeitung

  1. stirringby stirring at room temperature for 16 hours
  2. customthe crystal precipitated
  3. filtrationwas collected by filtration
  4. extractionthe filtrate was extracted with ethyl acetate
  5. washthe extract was washed with saturated saline
  6. dry with materialdried with magnesium sulfate
  7. concentrationThe dry product was concentrated under reduced pressure
  8. filtrationcollected by filtration
  9. washeluted with hexane:ethyl acetate (2:1)
  10. customThe desired fraction was collected
  11. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cdc95240a6dd4e28b54fac4a951b4ad1
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06248740B1

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