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

HRID 1369426Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1369426
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[C:8]1[S:9][CH:10]=[CH:11][CH:12]=1.[F:14][C:15]1[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=1[C:17]([NH:19][NH2:20])=O.Cl.C(N(CC)CC)C>CC1C=CC(C)=CC=1>[Cl:1][C:2]1[C:7]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:6][C:5]2[N:4]([C:17]([C:16]3[CH:21]=[CH:22][CH:23]=[CH:24][C:15]=3[F:14])=[N:19][N:20]=2)[N:3]=1

Komponenten

5

Edukt 3

HCID 11130Triethylamine hydrochlorideHCID 1362882-FluorobenzhydrazideHCID 226099503,6-Dichloro-4-(thien-2-yl)pyridazine

Produkt 1

HCID 226098966-Chloro-3-(2-fluorophenyl)-7-(thien-2-yl)-1,2,4-triazolo[4,3-b]pyridazineAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7809P-XyleneLösungsmittel

Versuchsvorschrift

A mixture of 3,6-dichloro-4-(thien-2-yl)pyridazine from above (0.5 g, 2.1 mmol), 2-fluorobenzhydrazide (0.66 g, 4,3 mmol) and triethylamine hydrochloride (0.59 g, 4,3 mmol) in p-xylene (10 ml) was stirred and heated at reflux under nitrogen for 30 hours. Upon cooling the volatiles were removed in vacuo. The residue was partly purified by chromatography on silica gel eluting with 50%→66%→100% ethyl acetate-hexane to give the title compound as a yellow solid (0.19 g, 26%). MS (ES+) m/e 331 [MH]+, 333 [MH]+. This material was used without further purification.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux under nitrogen for 30 hours
  3. temperatureUpon cooling the volatiles
  4. customwere removed in vacuo
  5. customThe residue was partly purified by chromatography on silica gel eluting with 50%→66%→100% ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-ca4609a0d96f4e4fbda64e55736a09d7
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06579875B1

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