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

HRID 2306586Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2306586
[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 33 1 [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-05f41e9359894802aa0397efa2f33191
Quelldatensatz
uspto-grants-2004_12
Patentnummer
US06828322B2

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