Ethanol → 3-(5-Isopropyl-2,4-bis-methoxymethoxyphenyl)-4-[4-(4-methylpiperazin-1-ylmethyl)phenyl]-5-methylsulfanyl-[1,2,4]triazole

5-(5-isopropyl-2,4-bis-methoxymethoxyphenyl)-4-[4-(4-methylpiperazin-1-ylmethyl)phenyl]-2,4-dihydro-[1,2,4]triazol-3-thione (F652-06, 3.17 g, 6.01 mmol) and potassium carbonate (829 mg, 6.00 mmol) were weighed and placed in a reaction vessel. After adding ethanol (30 mL), methyl iodide (0.374 mL, 6.01 mmol) was added to the mixture. After heating for 1 hour under reflux, the temperature was returned to room temperature, and the solvent was distilled off under reduced pressure. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and then filtered to remove sodium sulfate, and the solvent was distilled off under reduced pressure to obtain pale yellow foam. Diethyl ether was added to the foam and the insoluble material was removed by filtration. After washing with water, the filtrate was washed with saturated sodium chloride solution. The extract was dried with sodium sulfate, and sodium sulfate was removed by filtration. The solvent was distilled off under reduced pressure to obtain 3-(5-isopropyl-2,4-bis-methoxymethoxyphenyl)-4-[4-(4-methylpiperazin-1-ylmethyl)phenyl]-5-methylsulfanyl-[1,2,4]triazole (F652-07, pale yellow foam, 2.05 g, 63%).

1. customplaced in a reaction vessel
2. additionwas added to the mixture
3. temperatureAfter heating for 1 hour
4. temperatureunder reflux
5. customwas returned to room temperature
6. distillationthe solvent was distilled off under reduced pressure
7. additionTo the reaction mixture was added water
8. extractionthe mixture was extracted with ethyl acetate
9. washThe extract was washed with saturated sodium chloride solution
10. dry with materialdried over anhydrous sodium sulfate
11. filtrationfiltered
12. customto remove sodium sulfate
13. distillationthe solvent was distilled off under reduced pressure
14. customto obtain pale yellow foam
15. customthe insoluble material was removed by filtration
16. washAfter washing with water
17. washthe filtrate was washed with saturated sodium chloride solution
18. dry with materialThe extract was dried with sodium sulfate, and sodium sulfate
19. customwas removed by filtration
20. distillationThe solvent was distilled off under reduced pressure

ORD-Eintrag

ord-d09e514e1c38432e86b978456380eabe

Quelldatensatz

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08399464B2