Ethanol hydrochloride → HCID 68924115, compound

To 0.51 g of tert-butyl (1-(2-(7-bromo-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)(2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)carbamate, 18 mL of a 2 mol/L hydrogen chloride/ethanol solution was added at room temperature, the mixture was stirred at room temperature for 59 hours, and at 50° C. for 9 hours, and then, the generated solid was filtered off. Subsequently, the solid was suspended in 3 mL of chloroform, thereto was added 5 mL of trifluoroacetic acid, the mixture was stirred at room temperature for 100 minutes, and then the solvent was distilled off under reduced pressure. The residue was charged with 10 mL of chloroform and 3 mL of water and adjusted to pH 10 with a 2 mol/L aqueous sodium hydroxide solution, and then the organic layer was separated. The aqueous layer was extracted with chloroform twice, and combined with the organic layer, the resultant solution was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was dissolved in 2 mL of ethyl acetate and 3 mL of ethanol, and 10 mL of a 2 mol/L hydrochloric acid/ethanol solution was added thereto, the mixture was stirred for 15 minutes, and the solvent was distilled off under reduced pressure. To the residue, 4 mL of ethyl acetate was added and suspended, and the solid was filtered off to obtain 0.41 g of 7-bromo-1-(2-(4-((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)amino)piperidin-1-yl)ethyl)-1,5-naphthyridin-2(1H)-one hydrochloride as a slightly yellow solid.

1. waitat 50° C. for 9 hours
2. filtrationthe generated solid was filtered off
3. additionwas added 5 mL of trifluoroacetic acid
4. stirringthe mixture was stirred at room temperature for 100 minutes
5. distillationthe solvent was distilled off under reduced pressure
6. additionThe residue was charged with 10 mL of chloroform and 3 mL of water
7. customthe organic layer was separated
8. extractionThe aqueous layer was extracted with chloroform twice
9. washthe resultant solution was washed with a saturated aqueous sodium chloride solution
10. dry with materialdried over anhydrous magnesium sulfate
11. distillationthe solvent was distilled off under reduced pressure
12. dissolutionThe residue was dissolved in 2 mL of ethyl acetate
13. addition3 mL of ethanol, and 10 mL of a 2 mol/L hydrochloric acid/ethanol solution was added
14. stirringthe mixture was stirred for 15 minutes
15. distillationthe solvent was distilled off under reduced pressure
16. additionTo the residue, 4 mL of ethyl acetate was added
17. filtrationthe solid was filtered off

ORD record

ord-fb301077813547b98c6c7dacd7206c94

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367831B2