Hydrochloric Acid → HCID 22503011, compound

The resulting compound and 7-(1-ethylpiperazin-4-yl)-5-bromothieno[2,3-c]pyridine (0.19 g) were reacted in the same manner as in Example 300-4, to give a reaction solution containing 7-(4-ethylpiperazin-1-yl)-5-[4-(2-acetoxyethoxy)-3-chlorophenyl]thieno[2,3-c]pyridine. Ethyl acetate and 2N hydrochloric acid were added to the reaction solution, and the resulting insoluble matters were filtered off. The aqueous layer was separated, while the organic layer was extracted with 2N hydrochloric acid. The resulting aqueous layers were combined and washed with ethyl acetate twice. The pH of the resulting solution was adjusted to pH 10 by adding a 8N aqueous solution of sodium hydroxide, and then the solution was extracted with ethyl acetate twice. The extract was washed with brine, dried over magnesium sulfate, and the solvent was evaporated. Methanol (6 ml) was added to the resulting residue and dissolved, followed by the addition of a 8N aqueous solution of sodium hydroxide (0.75 ml). The resulting mixture was left as it was at room temperature for 45 min, and then the solvent was evaporated. Water was added to the resulting residue, and then the mixture was extracted with ethyl acetate thrice. The extract was washed with brine, dried over magnesium sulfate, and the solvent was evaporated. The resulting residue was purified by NH silica gel column chromatography (ethyl acetate/n-hexane system), to give the title compound (0.03 g) as a colorless viscous oil.

1. customto give a reaction solution
2. filtrationthe resulting insoluble matters were filtered off
3. customThe aqueous layer was separated, while the organic layer
4. extractionwas extracted with 2N hydrochloric acid
5. washwashed with ethyl acetate twice
6. additionby adding a 8N aqueous solution of sodium hydroxide
7. extractionthe solution was extracted with ethyl acetate twice
8. washThe extract was washed with brine
9. dry with materialdried over magnesium sulfate
10. customthe solvent was evaporated
11. additionMethanol (6 ml) was added to the resulting residue
12. dissolutiondissolved
13. additionfollowed by the addition of a 8N aqueous solution of sodium hydroxide (0.75 ml)
14. waitThe resulting mixture was left as it
15. customthe solvent was evaporated
16. additionWater was added to the resulting residue
17. extractionthe mixture was extracted with ethyl acetate thrice
18. washThe extract was washed with brine
19. dry with materialdried over magnesium sulfate
20. customthe solvent was evaporated
21. customThe resulting residue was purified by NH silica gel column chromatography (ethyl acetate/n-hexane system)

ORD record

ord-d3e7426c00da40e09c57c79dc61ba3e0

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06875761B2