Water → HCID 117761027, compound

Temperature

150 °C

The tert-butyl (2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-yl)carbamate (75 mg) obtained in (Example 3.15) <Step 4> and pyrrolidine (1 ml) were stirred under microwave heating at 150° C. for 1 hour. Thereafter, ethyl acetate (10 ml) and water (3 ml) were added to the reaction solution. An organic layer was separated, and was then dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure. Thereafter, potassium hydroxide (134 mg) was added to an ethanol (2 ml) solution of the obtained residue, and the obtained mixture was then heated to reflux for 16 hours. Thereafter, the solvent was distilled away under reduced pressure, and potassium hydroxide (134 mg) was added to an ethylene glycol (2 ml) solution of the obtained residue, followed by heating the obtained mixture at 155° C. for 2 hours. The solvent was distilled away under reduced pressure, and ethyl acetate (10 ml) and water (3 ml) were then added to the obtained residue. An organic layer was separated, and was then dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, and the obtained residue was then purified by silica gel column chromatography (silica gel:eluent; heptane:ethyl acetate=50:50-0:100) to obtain a crude product. The obtained crude product was dissolved in 4 N hydrochloric acid-ethyl acetate (1 ml), and the precipitated solid was then collected by filtration, so as to obtain the title compound (16 mg) in the form of a yellow solid.

1. customAn organic layer was separated
2. dry with materialwas then dried over anhydrous sodium sulfate
3. distillationThe solvent was distilled away under reduced pressure
4. additionThereafter, potassium hydroxide (134 mg) was added to an ethanol (2 ml) solution of the obtained residue
5. temperaturethe obtained mixture was then heated
6. temperatureto reflux for 16 hours
7. distillationThereafter, the solvent was distilled away under reduced pressure, and potassium hydroxide (134 mg)
8. additionwas added to an ethylene glycol (2 ml) solution of the obtained residue
9. temperatureby heating the obtained mixture at 155° C. for 2 hours
10. distillationThe solvent was distilled away under reduced pressure, and ethyl acetate (10 ml) and water (3 ml)
11. additionwere then added to the obtained residue
12. customAn organic layer was separated
13. dry with materialwas then dried over anhydrous sodium sulfate
14. distillationThe solvent was distilled away under reduced pressure
15. customthe obtained residue was then purified by silica gel column chromatography (silica gel:eluent; heptane:ethyl acetate=50:50-0:100)
16. customto obtain a crude product
17. customThe obtained crude product
18. filtrationthe precipitated solid was then collected by filtration

ORD record

ord-bd7c83ad9764402c9611453f39409209

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08980888B2