6-Amino-3-chloropyridazine → 6-([1,2,4]Triazolo[4,3-a]pyridin-3-ylthio)pyridazin-3-amine
Reaktionsgleichung
[N:1]1[N:2]=[C:3]([SH:10])[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.Cl[C:12]1[N:17]=[N:16][C:15]([NH2:18])=[CH:14][CH:13]=1>C(O)(=O)C>[N:1]1[N:2]=[C:3]([S:10][C:12]2[N:17]=[N:16][C:15]([NH2:18])=[CH:14][CH:13]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
A reaction mixture of [1,2,4]triazolo[4,3-a]pyridine-3-thiol (8.49 g, 55.0 mmol) and 6-chloropyridazin-3-amine (6.82 g, 50 mmol) in acetic acid (100 mL) was heated at 80° C. for 20 hrs. The reaction was stripped to dryness via rotary evaporation and the resulting material was suspended in H2O (100 mL). To this suspension, solid Na2CO3 was added in portions until pH 10 was achieved and then the mixture was sonicated. The resulting solid was collected by filtration and rinsed thoroughly with water followed by ethyl ether. The solid was dried in vacuum over P2O5 to provide the title compound, 6-([1,2,4]Triazolo[4,3-a]pyridin-3-ylsulfanyl)-pyridazin-3-ylamine, as a white power (11.0 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.15-7.25 (m, 1 H) 7.53-7.58 (m, 1 H) 7.61 (ddd, J=9.22, 6.69, 1.26 Hz, 1 H) 7.84-7.90 (m, 1 H) 7.99 (dt, J=9.09, 1.01 Hz, 1 H) 8.51 (dt, J=7.01, 1.04 Hz, 1 H) 8.79 (br. s., 2 H). ESI-MS:m/z 553.2 (M+H)+.