Triethylamine → N-[3-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)phenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide

To a solution of N-{3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]phenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide (117 mg, 0.322 mmol) and triethylamine (134 μL, 0.966 mmol) in tetrahydrofuran (5 mL) was added with stirring under ice-cooling cyclopropanecarbonyl chloride (38.0 μL, 0.419 mmol), and the mixture was stirred at room temperature for 12 hr. Cyclopropanecarbonyl chloride (29.3 μL, 0.322 mmol) was further added and the mixture was stirred for 3 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, sodium carbonate (100 mg), methanol (2 mL) and water (100 μL) were added to the residue, and the mixture was stirred at 50° C. for 30 min. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate) and recrystallized from ethyl acetate to give the title compound (112 mg, 60%) as a white solid.

1. stirringthe mixture was stirred at room temperature for 12 hr
2. stirringthe mixture was stirred for 3 hr
3. extractionextracted with ethyl acetate
4. washThe organic layer was washed with water and saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltrated
7. concentrationThe filtrate was concentrated under reduced pressure, sodium carbonate (100 mg), methanol (2 mL) and water (100 μL)
8. additionwere added to the residue
9. stirringthe mixture was stirred at 50° C. for 30 min
10. additionThe reaction mixture was diluted with water
11. extractionextracted with ethyl acetate
12. washThe organic layer was washed with water and saturated brine
13. dry with materialdried over anhydrous magnesium sulfate
14. filtrationfiltrated
15. concentrationThe filtrate was concentrated under reduced pressure
16. customthe residue was purified by column chromatography (silica gel, ethyl acetate)
17. customrecrystallized from ethyl acetate

ORDレコード

ord-f355ac10b6874dc2bdb4f03cc7e651a0

出典データセット

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08304557B2