Hydrochloric Acid → HCID 22172758, compound

A mixture of 8-(ethoxymethyl)-7-(2-methylpropyl)-5-methyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridine (6.5 g, 22.5 mmol), triphenylphosphine (6.5 g, 24.8 mmol), and toluene (130 mL) was stirred and heated at reflux under nitrogen for 24 hours. Additional triphenylphosphine (3.0 g, 11.4 mmol) was added to the cloudy mixture, and the reaction was continued for three days. The solvent was removed under reduced pressure, and the resulting brown oil was dissolved in methanol (100 mL). Following the addition of a 1.0 M solution of hydrochloric acid in diethyl ether (45 mL) to the methanol solution, the reaction was heated at reflux overnight. The solvents were removed under reduced pressure, and water (200 mL) was added to the resulting brown oil, forming a white precipitate that was removed by filtration. Solid sodium carbonate (6.5 g) was added to the aqueous solution, followed by extraction with dichloromethane (2×200 mL). The combined extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide a brown oil, which was dissolved in 2-propanol (45 mL). A 1.0 M solution of hydrochloric acid in diethyl ether (22.5 mL) was added to the solution of crude product, and a white solid formed. After one hour the solid was isolated by filtration, washed with cold 2-propanol and diethyl ether, and dried in a vacuum oven at 90° C. for two days to yield 4.3 g of 2-(ethoxymethyl)-1-(2-methylpropyl)-6-methyl-1H-imidazo[4,5-c]pyridin-4-amine hydrochloride as a white solid, m.p. 181–183° C.

1. temperatureheated
2. temperatureat reflux under nitrogen for 24 hours
3. customThe solvent was removed under reduced pressure
4. dissolutionthe resulting brown oil was dissolved in methanol (100 mL)
5. additionthe addition of a 1.0 M solution of hydrochloric acid in diethyl ether (45 mL) to the methanol solution
6. temperaturethe reaction was heated
7. temperatureat reflux overnight
8. customThe solvents were removed under reduced pressure, and water (200 mL)
9. additionwas added to the resulting brown oil
10. customforming a white precipitate that
11. customwas removed by filtration
12. additionSolid sodium carbonate (6.5 g) was added to the aqueous solution
13. extractionfollowed by extraction with dichloromethane (2×200 mL)
14. dry with materialThe combined extracts were dried over magnesium sulfate
15. filtrationfiltered
16. concentrationconcentrated under reduced pressure
17. customto provide a brown oil, which
18. customa white solid formed
19. customAfter one hour the solid was isolated by filtration
20. washwashed with cold 2-propanol and diethyl ether
21. customdried in a vacuum oven at 90° C. for two days

ORD record

ord-693100cc6e76475ebed0935e8330d11a

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07038053B2