反应详情

5-amino-3-((3-chlorophenyl)amino)-1H-pyrazole-4-carboxamide (300 mg) was suspended in EtOH (5 mL) and 4-[{5-(Trifluoromethyl)pyridin-2-yl}oxy]benzaldehyde (318 mg, 1 eq.) and piperidine (3 drops) were added. Stirred at reflux until intermediate was absent (HPLC). After reaction was complete (18 hrs) it was brought to room temperature and filtered to obtain product as a yellow powder. Powder was washed with EtOH. Product was allowed to dry under vacuum for 1 hr (360 mg, 60% yield). Resulting imine (360 mg) was suspended in 10 mL MeOH and sodium borohydride (10 eq., 272 mg) was added. HPLC confirmed reaction was complete (absence of imine). After completion (1 hr), precipitate was filtered to obtain D33 as a light yellow powder. Product was washed with deionized water to remove excess sodium borohydride. Product was allowed to dry under vacuum for 18 hrs. 255 mg (70% yield) of final product was obtained.

1. temperatureat reflux until intermediate
2. customAfter reaction
3. custom(18 hrs) it
4. customwas brought to room temperature
5. filtrationfiltered
6. customto obtain product as a yellow powder
7. washPowder was washed with EtOH
8. customto dry under vacuum for 1 hr (360 mg, 60% yield)
9. customreaction
10. filtrationAfter completion (1 hr), precipitate was filtered
11. customto obtain D33 as a light yellow powder
12. washProduct was washed with deionized water
13. customto remove excess sodium borohydride
14. customto dry under vacuum for 18 hrs