3,5-Difluorobenzaldehyde 2-(6-chloro-5-cyclobutyl-3-pyridazinyl)hydrazone → 6-Chloro-7-cyclobutyl-3-(3,5-difluorophenyl)-1,2,4-triazolo[4,3-b]pyridazine

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Reaktionsgleichung

[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][N:9]=[CH:10][C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=2)=[CH:4][C:3]=1[CH:19]1[CH2:22][CH2:21][CH2:20]1>C(O)C>[Cl:1][C:2]1[C:3]([CH:19]2[CH2:20][CH2:21][CH2:22]2)=[CH:4][C:5]2[N:6]([C:10]([C:11]3[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=3)=[N:9][N:8]=2)[N:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

Ferric chloride (3.423 g, 12.66 mmol) in ethanol (15 ml) was added dropwise to a solution of N-(6-chloro-5-cyclobutylpyridazin-3-yl)-N′-(3,5-difluorobenzylidene)hydrazine (0.816 g, 2.53 mmol) in ethanol (35 ml) and heated at 70° C. After 3 hours the reaction mixture was partitioned between dichloromethane (250 ml) and brine (250 ml). The organic phase was dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica gel, eluting with ethyl acetate-hexane mixtures to afford the title pyridazite (0.51 g, 63%). 1H NMR (250 MHz, CDCl3) 1.84-2.08 (1H, m), 2.08-2.36 (3H, m), 2.42-2.68 (2H, m), 3.65-3.87 (1H, m), 6.88-7.06 (1H, m), 8.01 (1H, s), 8.04-8.21 (2H, m). MS (ES+) 321 [MH]+, 323 [MH]+.

Aufarbeitung

customAfter 3 hours the reaction mixture was partitioned between dichloromethane (250 ml) and brine (250 ml)
dry with materialThe organic phase was dried (MgSO4)
filtrationfiltered
customevaporated
customThe residue was purified by chromatography on silica gel
washeluting with ethyl acetate-hexane mixtures
customto afford the title pyridazite (0.51 g, 63%)

Quellen und Nachweise

ORD-Eintrag: ord-c4e0680619ec45449fa88a0ca1b4a3d6
Quelldatensatz: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06579875B1

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