Ammonia → HCID 178418385, compound

A solution of the above acid chloride (ca. 0.02M) in tetrahydrofuran (10 ml) was added over 8 minutes to a stirred solution of 7-aminobenzotriazole (2.5 g, 0.019M) in pyridine (20 ml). The mixture was stirred at room temperature for 4 hours, then 0.88M ammonia (0.5 ml) was added and stirring was continued for another 20 minutes. The mixture was poured into ice/water (200 ml) to give an oil which soon solidified. 10M Hydrochloric acid (25 ml) was added and the acidified mixture was stirred for 5 minutes before the resulting pink solid was filtered off, washed with water and dried, 5.8 g. The solid was added to methanol (25 ml) and the suspension was stirred at room temperature for 1 hour. Filtration of the mixture resulted in removal of most of the colour from the solid, which was further washed with methanol and dried, 4.3 g. The solid was heated briefly on a steam-bath with tetrahydrofuran (50 ml) to give a cloudy solution. This was cooled and filtered through Kieselguhr and the filtrate was concentrated under reduced pressure to leave an off-white solid. Methanol (25 ml) was added and the mixture was stirred at room temperature for 2 hours, then the resulting white solid was filtered off, washed with methanol and dried to give B1-1, 15 g (52%). The positive and negative ion electrospray mass spectra were consistent with the structure of the required product. LCMS indicated purity of >98%, which was also supported by the 1H-nmr spectrum.

1. stirringstirring
2. waitwas continued for another 20 minutes
3. customto give an oil which
4. stirringthe acidified mixture was stirred for 5 minutes before the resulting pink solid
5. filtrationwas filtered off
6. washwashed with water
7. customdried
8. additionThe solid was added to methanol (25 ml)
9. stirringthe suspension was stirred at room temperature for 1 hour
10. filtrationFiltration of the mixture
11. customresulted in removal of most of the colour from the solid, which
12. washwas further washed with methanol
13. customdried
14. temperatureThe solid was heated briefly on a steam-bath with tetrahydrofuran (50 ml)
15. customto give a cloudy solution
16. temperatureThis was cooled
17. filtrationfiltered through Kieselguhr
18. concentrationthe filtrate was concentrated under reduced pressure
19. customto leave an off-white solid
20. stirringthe mixture was stirred at room temperature for 2 hours
21. filtrationthe resulting white solid was filtered off
22. washwashed with methanol
23. customdried
24. customto give B1-1, 15 g (52%)

ORD record

ord-6b8028e1c59849e99f9696f10ec23a8b

Source dataset

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06589724B1