Nitric Acid → HCID 54224790, compound

3.6 g (12.7 mmol) 5-Amino-1-(3-bromo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)pyrazole was suspended in 15 ml acetic acid and treated with 1.23 ml (13.0 mmol) acetic anhydride. The mixture was stirred for 5 hours at room temperature. 1.5 ml (15.9 mmol) acetic anhydride was added and then, with ice-bath cooling, 0.66 ml (15.5 mmol) fuming nitric acid was added, dropwise. After stirring for 12 hours at room temperature, the mixture was concentrated. The residue was dissolved in 30 ml ethanol and treated with 11.2 ml concentrated hydrochloric acid. After heating for 3 hours under reflux, the mixture was concentrated and the residue taken up in water and ethyl acetate. It was made basic with 2N aqueous sodium hydroxide and the organic phase separated. The aqueous phase was extracted twice with ethyl acetate. The combined organic phases were washed once with water and once with saturated aqueous sodium chloride. The organic phase was dried and concentrated. The residue was recrystallised from ethyl acetate.

1. temperaturewith ice-bath cooling
2. additionwas added
3. stirringAfter stirring for 12 hours at room temperature
4. concentrationthe mixture was concentrated
5. dissolutionThe residue was dissolved in 30 ml ethanol
6. additiontreated with 11.2 ml concentrated hydrochloric acid
7. temperatureAfter heating for 3 hours
8. temperatureunder reflux
9. concentrationthe mixture was concentrated
10. customthe organic phase separated
11. extractionThe aqueous phase was extracted twice with ethyl acetate
12. washThe combined organic phases were washed once with water and once with saturated aqueous sodium chloride
13. customThe organic phase was dried
14. concentrationconcentrated
15. customThe residue was recrystallised from ethyl acetate

ORD record

ord-a7cf579ae1cd4945b6d04b66f9c50f86

Source dataset

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05869686