1,1-Dichloroethane → 2-Chloro-6-propylimidazo[1,2-b]pyridazine-3-sulfonamide

2-Chloro-6-n-propylimidazo[1,2-b]pyridazine (0.8 g, 4.1 mmol) and dichloroethane (10 ml) were introduced into a 200-ml eggplant type flask and stirred at room temperature, and chlorosulfonic acid (0.54 g, 4.5 mmol) was added thereto all at once, and the mixture was stirred for 4 hours under reflux with heating. The reaction solution was cooled to about 70° C., and triethylamine (0.5 g, 5 mmol) was added thereto all at once and stirred until the solid was dissolved, and phosphorus oxychloride (0.79 g, 5 mmol) was added thereto all at once, and the mixture was stirred for 2 hours under reflux with heating. After the reaction was completed, the reaction solution was left to cool, and water (50 ml) was added thereto and the organic phase was separated. The organic phase was washed with a saturated saline, dried over magnesium sulfate and concentrated. Acetonitrile (10 ml) and 28% ammonia water (4 ml) were added to the residue and stirred at room temperature for 2 hours. After the reaction was completed, water (100 ml) was added to the reaction solution, which was then adjusted to about pH 2 with dilute hydrochloric acid, and the formed crystals were collected by filtration, washed with water and chloroform, and dried under reduced pressure to give the title compound as pale brown crystals. The yield was 0.49 g (43.5%).

1. stirringall at once, and the mixture was stirred for 4 hours
2. temperatureunder reflux
3. temperaturewith heating
4. temperatureThe reaction solution was cooled to about 70° C.
5. stirringall at once and stirred until the solid
6. dissolutionwas dissolved
7. stirringall at once, and the mixture was stirred for 2 hours
8. temperatureunder reflux
9. temperaturewith heating
10. waitthe reaction solution was left
11. temperatureto cool
12. customthe organic phase was separated
13. washThe organic phase was washed with a saturated saline
14. dry with materialdried over magnesium sulfate
15. concentrationconcentrated
16. additionAcetonitrile (10 ml) and 28% ammonia water (4 ml) were added to the residue
17. stirringstirred at room temperature for 2 hours
18. additionwater (100 ml) was added to the reaction solution, which
19. filtrationthe formed crystals were collected by filtration
20. washwashed with water and chloroform
21. customdried under reduced pressure

ORDレコード

ord-92520492ff4b4a2bb89df89910de007a

出典データセット

uspto-grants-2007_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07307165B2