Triethylamine hydrochloride → 7-Tert-butyl-6-chloro-3-(2-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine

HRID 986913

Reaktionsgleichung

Reaktionsgleichung von HRID 986913
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[C:8]([CH3:11])([CH3:10])[CH3:9].[F:13][C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[C:16]([NH:18][NH2:19])=O.Cl.C(N(CC)CC)C>O1CCOCC1>[Cl:1][C:2]1[C:7]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:6][C:5]2[N:4]([C:16]([C:15]3[CH:20]=[CH:21][CH:22]=[CH:23][C:14]=3[F:13])=[N:18][N:19]=2)[N:3]=1

Komponenten

5

Edukt 3

HCID 11130Triethylamine hydrochlorideHCID 898464-tert-Butyl-3,6-dichloropyridazineHCID 1362882-Fluorobenzhydrazide

Produkt 1

HCID 111508847-Tert-butyl-6-chloro-3-(2-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazineAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 3,6-dichloro-4-(1,1-dimethylethyl)pyridazine (20 g, 0.097 mol), 2-fluorobenzhydrazide (22.6 g, 0.145 mol) and triethylamine hydrochloride (20 g, 0.0145 mol) in dioxan (1.2 l) was stirred and heated at reflux under a stream of nitrogen for 4 days. Upon cooling the volatiles were removed in vacuo and the residue was triturated with dichloromethane (200 ml), filtered and concentrated under vacuum. The residue was purified by chromatography on silica gel eluting with 0%→25% ethyl acetate/dichloromethane to give the title compound (12.95 g. 44%) as a white solid. Data for the title compound: 1H NMR (360 MHz, CDCl3) δ1.57 (9H, s), 7.26-7.35 (2H, m), 7.53-7.60 (1H, m), 7.89-7.93 (1H, m), 8.17 (1H, s); MS (ES+) m/e 305 [MH]+, 307 [MH]+.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux under a stream of nitrogen for 4 days
  3. temperatureUpon cooling the volatiles
  4. customwere removed in vacuo
  5. customthe residue was triturated with dichloromethane (200 ml)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by chromatography on silica gel eluting with 0%→25% ethyl acetate/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-32f104141f544d779861034672e1535e
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06630471B1

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