Triethylamine hydrochloride → 6-Chloro-7-cyclobutyl-3-phenyl-1,2,4-triazolo[4,3-b]pyridazine

HRID 277327

Reaktionsgleichung

Reaktionsgleichung von HRID 277327
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[CH:8]1[CH2:11][CH2:10][CH2:9]1.[C:13]([NH:21][NH2:22])(=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.C(N(CC)CC)C>CC1C=CC(C)=CC=1>[Cl:1][C:2]1[C:7]([CH:8]2[CH2:11][CH2:10][CH2:9]2)=[CH:6][C:5]2[N:4]([C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:21][N:22]=2)[N:3]=1

Komponenten

5

Edukt 3

HCID 11130Triethylamine hydrochlorideHCID 11955BenzoylhydrazineHCID 219732193,6-Dichloro-4-cyclobutylpyridazine

Produkt 1

HCID 110005936-Chloro-7-cyclobutyl-3-phenyl-1,2,4-triazolo[4,3-b]pyridazineAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7809P-XyleneLösungsmittel

Versuchsvorschrift

A mixture of 3,6-dichloro-4-cyclobutylpyridazine from above (55.7 g, 0.27 mol), benzoic hydrazide (41.1 g, 0.30 mol) and triethylamine hydrochloride (41.5 g, 0.30 mol) in p-xylene (0.4 l) was stirred and heated at reflux under a stream of nitrogen for 24 hours. Upon cooling the volatiles were removed in vacuo. The residue was partitioned between dichloromethane and water. The aqueous was basified by the addition of solid potassium carbonate. Some dark insoluble material was removed by filtration at this stage. The aqueous phase was further extracted with dichloromethane (x2). The combined extracts were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica gel eluting with 5%→10%→25% ethyl acetate/dichloromethane to give the title compound, (26.4 g, 34%) as an off-white solid. Data for the title compound: 1H NMR (360 MHz, CDCl3) δ 1.90-2.00 (1H, m), 2.12-2.28 (3H, m), 2.48-2.57 (2H, m), 3.69-3.78 (1H, m), 7.49-7.59 (3H, m), 7.97 (1H, s), 8.45-8.48 (2H, m); MS (ES+) m/e 285 [MH]+, 287 [MH]+.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux under a stream of nitrogen for 24 hours
  3. temperatureUpon cooling the volatiles
  4. customwere removed in vacuo
  5. customThe residue was partitioned between dichloromethane and water
  6. additionThe aqueous was basified by the addition of solid potassium carbonate
  7. customSome dark insoluble material was removed by filtration at this stage
  8. extractionThe aqueous phase was further extracted with dichloromethane (x2)
  9. dry with materialThe combined extracts were dried (MgSO4)
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was purified by chromatography on silica gel eluting with 5%→10%→25% ethyl acetate/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-202aa9682de447a79f20c99eabcb42bc
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355798B1

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