1-Butyl-3-methylimidazolium hexafluorophosphate → N*6*,N*6*-Diethyl-7,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazine-3,6-diamine

HRID 657875

Reaktionsgleichung

Reaktionsgleichung von HRID 657875
Cl[C:2]1[C:3]([CH3:13])=[C:4]([CH3:12])[C:5]2[N:6]([C:8]([NH2:11])=[N:9][N:10]=2)[N:7]=1.F[P-](F)(F)(F)(F)F.[CH2:21]([N+:25]1[CH:29]=[CH:28]N(C)C=1)[CH2:22]CC>C(NCC)C>[CH2:21]([N:25]([CH2:29][CH3:28])[C:2]1[C:3]([CH3:13])=[C:4]([CH3:12])[C:5]2[N:6]([C:8]([NH2:11])=[N:9][N:10]=2)[N:7]=1)[CH3:22]

Komponenten

4

Edukt 2

HCID 27341741-Butyl-3-methylimidazolium hexafluorophosphateHCID 580458046-Chloro-7,8-dimethyl-[1,2,4]triazolo[4,3-B]pyridazin-3-amine

Produkt 1

HCID 58045894N*6*,N*6*-Diethyl-7,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazine-3,6-diamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8021DiethylamineLösungsmittel

Versuchsvorschrift

6-Chloro-7,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine (W2.006a, 800 mg and 650 mg divided between 2 microwave vessels) was initially charged each dissolved in 12 ml of diethylamine and admixed with 1-butyl-3-methylimidazolium hexafluorophosphate (150 μl). Subsequently, they were placed into the microwave at 180° C. for 4 h. In order to complete the reaction, they were placed again into the microwave at 180° C. for 4 h and then left to stand overnight. The two reaction mixtures were combined in a round-bottom flask and dried. The residue was admixed with water and extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated. The residue was purified by means of preparative HPLC (met. F), 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. 900 mg of the title compound were obtained.

Aufarbeitung

  1. customthe reaction, they
  2. waitwere placed again into the microwave at 180° C. for 4 h
  3. waitleft
  4. waitto stand overnight
  5. customThe two reaction mixtures
  6. customwere combined in a round-bottom flask
  7. customdried
  8. extractionextracted three times with dichloromethane
  9. dry with materialThe combined organic phases were dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified by means of preparative HPLC (met. F)
  13. extractionextracted repeatedly with dichloromethane
  14. dry with materialThe combined organic phases were dried over sodium sulfate
  15. filtrationfiltered
  16. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-cf89ee8961294bbca38c75059dd07309
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076336B2

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