Triethylamine hydrochloride → 6-Chloro-7-phenyl-3-(pyrazin-2-yl)-1,2,4-triazolo[4,3-b]pyridazine

HRID 378834

Reaktionsgleichung

Reaktionsgleichung von HRID 378834
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[N:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[C:21]([NH:23][NH2:24])=O.Cl.C(N(CC)CC)C>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][C:5]2[N:4]([C:21]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][N:15]=3)=[N:23][N:24]=2)[N:3]=1

Komponenten

5

Edukt 3

HCID 11130Triethylamine hydrochlorideHCID 258796Pyrazine-2-Carboxylic Acid HydrazideHCID 113220803,6-Dichloro-4-phenylpyridazine

Produkt 1

HCID 184306846-Chloro-7-phenyl-3-(pyrazin-2-yl)-1,2,4-triazolo[4,3-b]pyridazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

The product from Example 1 step b) (1 g, 4.46 mmol) was suspended in xylene (25 ml) with pyrazine-2-hydrazide (074 g, 5.35 mmol) and triethylamine hydrochloride (0.61 g, 4.46 mmol) and the reaction mixture was heated at reflux for 2 days. The solvent was removed under high vacuum, and the residue was dissolved in dichloromethane, basified with sodium bicarbonate and the aqueous extracted with dichloromethane (2×150 ml). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated. The residue was purified by silica gel chromatography using 0-40% ethyl acetate in dichloromethane as eluent to give the required product (0.249 g). 1H NMR (250 MHz, DMSO) δ 7.56 (5H, m), 8.43 (1H, s), 8.87 (1H, d, J=2.5 Hz), 8.96 (1H, d, J=2.5 Hz), 9.49 (1H, d J=2.5 Hz); MS (ES+) m/e 309 [MH+].

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 2 days
  3. customThe solvent was removed under high vacuum
  4. dissolutionthe residue was dissolved in dichloromethane
  5. extractionthe aqueous extracted with dichloromethane (2×150 ml)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-94be084a9c4c44ba99e51de48a7c48c4
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06297235B1

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