Trifluoroacetic acid → 6-Chloro-2-cyclopropylimidazo[1,2-b]pyridazine-3-carbaldehyde

HRID 1926782Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1926782
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH:11]3[CH2:13][CH2:12]3)[N:10]=2)[N:7]=1.FC(F)(F)[C:16](O)=[O:17]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:16]=[O:17])=[C:9]([CH:11]3[CH2:13][CH2:12]3)[N:10]=2)[N:7]=1

Komponenten

3

Edukt 2

HCID 6422Trifluoroacetic acidHCID 536291716-Chloro-2-cyclopropylimidazo[1,2-b]pyridazine

Produkt 1

HCID 577430506-Chloro-2-cyclopropylimidazo[1,2-b]pyridazine-3-carbaldehydeAusbeute 45 %

Versuchsvorschrift

6-chloro-2-cyclopropylimidazo[1,2-b]pyridazine x105 (1.88 g, 9.71 mmol) and hexamethyltetramine (HMTE, 13.61 g, 97.09 mmol, 10 eq) in trifluoroacetic acid (75 ml) are heated at 60° C. during 6 days. After cooling and solvent evaporation under reduced pressure, the crude product is dissolved in dichloromethane (150 ml). The organic layer is washed with water (150 ml) and the resulting aqueous layer is extracted with dichloromethane (150 ml). The cumulated organic layers are dried over MgSO4, filtered and the solvent is removed by evaporation under reduced pressure. The resulting crude compound is purified by preparative chromatography (benzine/AcOEt:80/20) affording 0.82 g of 6-chloro-2-cyclopropylimidazo[1,2-b]pyridazine-3-carbaldehyde x110.

Aufarbeitung

  1. temperatureAfter cooling
  2. customsolvent evaporation under reduced pressure
  3. dissolutionthe crude product is dissolved in dichloromethane (150 ml)
  4. washThe organic layer is washed with water (150 ml)
  5. extractionthe resulting aqueous layer is extracted with dichloromethane (150 ml)
  6. dry with materialThe cumulated organic layers are dried over MgSO4
  7. filtrationfiltered
  8. customthe solvent is removed by evaporation under reduced pressure
  9. customThe resulting crude compound is purified by preparative chromatography (benzine/AcOEt:80/20)

Quellen und Nachweise

ORD-Eintrag
ord-96c67fa1e55d482fa5b21e32316bda4d
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183241B2

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