3-Pentanol → 6-(1-Ethylpropoxy)-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

HRID 1524452Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1524452
[H-].[Na+].FC(F)(F)C(O)=O.Cl[C:11]1[CH:12]=[C:13]([CH3:21])[C:14]2[N:15]([C:17]([NH2:20])=[N:18][N:19]=2)[N:16]=1.[CH3:22][CH2:23][CH:24]([OH:27])[CH2:25][CH3:26]>CN(C=O)C>[CH2:23]([CH:24]([O:27][C:11]1[CH:12]=[C:13]([CH3:21])[C:14]2[N:15]([C:17]([NH2:20])=[N:18][N:19]=2)[N:16]=1)[CH2:25][CH3:26])[CH3:22]

Komponenten

5

Edukt 3

HCID 114283-Pentanol2×HCID 24758Sodium hydrideHCID 866507956-Chloro-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine trifluoroacetate

Produkt 1

HCID 580459026-(1-Ethylpropoxy)-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3-Pentanol (10.2 ml) was initially charged at RT with stirring and cooled almost to 0° C. with an ice bath. Subsequently, the mixture was admixed with portions of sodium hydride (511 mg). The suspension formed was heated to 55° C. for 30 min and admixed with portions of 6-chloro-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine trifluoroacetate (W2.002b; 500 mg), suspended in 3-pentanol (5 ml) and DMF (10 ml). After stirring at 55° C. for 1.5 h, the mixture was left to stand at RT overnight, the DMF was removed under reduced pressure, and the residue was then admixed with water and extracted four times with dichloromethane. The combined organic phases were dried over sodium sulfate and, after the desiccant had been filtered off, dried under reduced pressure. The residue was purified by means of preparative HPLC (met. A), and the clean product fractions were combined, freed of the acetonitrile under reduced pressure, alkalized with saturated potassium carbonate solution and extracted repeatedly with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated. 198 mg of the title compound were obtained.

Aufarbeitung

  1. customThe suspension formed
  2. temperaturewas heated to 55° C. for 30 min
  3. stirringAfter stirring at 55° C. for 1.5 h
  4. waitthe mixture was left
  5. customthe DMF was removed under reduced pressure
  6. extractionextracted four times with dichloromethane
  7. dry with materialThe combined organic phases were dried over sodium sulfate
  8. filtrationafter the desiccant had been filtered off
  9. customdried under reduced pressure
  10. customThe residue was purified by means of preparative HPLC (
  11. extractionextracted repeatedly with dichloromethane
  12. dry with materialThe combined organic phases were dried over sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2602351ec32d44bbbf61fef1cd966d38
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079906B2

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