Hydrochloric Acid → HCID 22503064, compound

HRID 1007047Notes

Reaction equation

HRID 1007047 reaction equation
C(N1CCN(C2N=[C:11](Br)[CH:12]=[C:13]3[CH:17]=[CH:16]SC=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]([CH2:42][O:43]C(=O)CC4CCCCC4)=[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:53].[C:54](OCC)(=O)C>>[ClH:53].[ClH:53].[CH2:19]([N:21]1[CH2:22][CH2:23][N:24]([C:27]2[N:28]=[C:29]([C:36]3[CH:37]=[CH:38][C:39]([CH:42]([CH:11]4[CH2:12][CH2:13][CH2:17][CH2:16][CH2:54]4)[OH:43])=[CH:40][CH:41]=3)[CH:30]=[C:31]3[CH:35]=[CH:34][S:33][C:32]=23)[CH2:25][CH2:26]1)[CH3:20]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 22503037HCID 22503037, compoundHCID 22503093HCID 22503093, compound

Product 1

HCID 22503064HCID 22503064, compound

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-1-yl)-5-[4-(cyclohexylacetoxymethyl)phenyl]thieno[2,3-c]pyridine. To the resulting reaction solution were added ethyl acetate and 2N hydrochloric acid, and then the resulting insoluble matters were filtered off. The aqueous layer was separated, while the organic phase was extracted with 2N hydrochloric acid. The resulting aqueous layers were combined and washed twice with ethyl acetate. The pH of the resulting solution was adjusted to pH 10 by adding 8N sodium hydroxide thereto, and then the solution was extracted with ethyl acetate twice. After washing with brine and drying over magnesium sulfate, the solvent was evaporated. Methanol (10 ml) was added to the resulting residue, dissolved, and then a 5N aqueous solution of sodium hydroxide (1 ml) was added thereto. The resulting solution was left as it was at room temperature for 1 hr, and then the solvent was evaporated. Water was added thereto, and then the mixture was extracted with ethyl acetate thrice. After washing with brine and drying over magnesium sulfate, the solvent was evaporated. The resulting residue was purified by NH silica gel column chromatography (ethyl acetate/n-hexane system), to give 0.12 g of the free compound of the title compound as a colorless amorphous.

Workup

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

Sources & evidence

ORD record
ord-825b1f24163c4378b7f128513af54294
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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