Acetic Anhydride → 2-(3-(5-Methyl-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-b]pyridazine

HRID 251807Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 251807
[N:1]1[C:2]([C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[C:13]#[N:14])=[CH:3][N:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[N:5]2.[NH2:18][OH:19].Cl.CCN([CH2:26][CH3:27])CC.C(OC(=O)C)(=O)C>CCO.CN(C1C=CN=CC=1)C.C1COCC1>[CH3:27][C:26]1[O:19][N:18]=[C:13]([C:12]2[CH:11]=[C:10]([C:2]3[N:1]=[C:9]4[CH:8]=[CH:7][CH:6]=[N:5][N:4]4[CH:3]=3)[CH:17]=[CH:16][CH:15]=2)[N:14]=1

Komponenten

8

Edukt 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 534394773-(Imidazo[1,2-b]pyridazin-2-yl)benzonitrile

Produkt 1

HCID 252558392-(3-(5-Methyl-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-b]pyridazine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 0.5 mmol 3-(imidazo[1,2-b]pyridazin-2-yl)benzonitrile, 1 mmol NH2OH.HCl and 1 mmol Et3N in EtOH were stirred at reflux for 4 h then cooled. Excess of solvent was removed in vacuo to afford the crude product. Acetic anhydride (2 mmol) was added to the mixture solution of the crude product, THF (15 ml), and DMAP (cat.) at room temperature and then the mixture was heated to reflux for 12 h. The mixture was concentrated in vacuo and the crude product was purified by column chromatography on silica gel to give the 2-(3-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-b]pyridazine.

Aufarbeitung

  1. temperatureat reflux for 4 h
  2. temperaturethen cooled
  3. customExcess of solvent was removed in vacuo
  4. customto afford the crude product
  5. temperaturethe mixture was heated
  6. temperatureto reflux for 12 h
  7. concentrationThe mixture was concentrated in vacuo
  8. customthe crude product was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-61aef1c968e7479ba86760a4ada59498
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868001B2

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