Hydrochloric Acid → HCID 22503537, compound

HRID 1814601Notes

Reaction equation

HRID 1814601 reaction equation
C(N1CCN(C2N=C(Br)C=C3C=CSC=23)CC1)C.[CH2:19]([N:21]1[CH2:26][CH2:25][N:24]([C:27]2[N:28]=[C:29]([C:36]3[CH:41]=[CH:40][C:39]([C:42]([CH3:50])([CH3:49])[CH2:43][CH2:44][O:45]C(=O)C)=[CH:38][CH:37]=3)[CH:30]=[C:31]3[CH:35]=[CH:34][S:33][C:32]=23)[CH2:23][CH2:22]1)[CH3:20].[ClH:51]>C(OCC)(=O)C>[ClH:51].[ClH:51].[CH2:19]([N:21]1[CH2:26][CH2:25][N:24]([C:27]2[N:28]=[C:29]([C:36]3[CH:41]=[CH:40][C:39]([C:42]([CH3:49])([CH3:50])[CH2:43][CH2:44][OH:45])=[CH:38][CH:37]=3)[CH:30]=[C:31]3[CH:35]=[CH:34][S:33][C:32]=23)[CH2:23][CH2:22]1)[CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 22503093HCID 22503093, compoundHCID 22503147HCID 22503147, compound

Product 1

HCID 22503537HCID 22503537, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The resulting compound and 7-(1-ethylpiperazin-4-yl)-5-bromothieno[2,3-c]pyridine (0.20 g) were reacted in the same manner as in Example 300-4, to give a reaction solution containing 7-(4-ethylpiperazin-1yl)-5-[4-(3-acetoxy-1,1-dimethylpropyl)phenyl]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 hydrochloride acid. The 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 thereto, and the solution was extracted with ethyl acetate twice. The extract was washed with brine, dried over magnesium sulfate, and the solvent was evaporated. Methanol (10 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 solution was left as it was at room temperature for 2 hr, 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 0.16 g of the free compound of the title compound as a colorless viscous oil.

Workup

  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 hydrochloride 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 (10 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 solution 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)

Sources & evidence

ORD record
ord-acbbeae14c504562a2cd335886f62863
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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