Hydrochloric Acid → HCID 22503343, compound

HRID 1251279Notes

Reaction equation

HRID 1251279 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]([O:42][CH2:43][C@H:44]([O:46]C(=O)C)[CH3:45])=[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].[ClH:50]>C(OCC)(=O)C>[ClH:50].[ClH:50].[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]([O:42][CH2:43][CH:44]([OH:46])[CH3:45])=[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 69179523HCID 69179523, compound

Product 1

HCID 22503343HCID 22503343, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The resulting compound and 7-(1-ethylpiperazin-4-yl)-5-bromothieno[2,3-c]pyridine (0.29 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-(R)-acetoxypropoxy]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 hydrochloric 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 subsequently, methanol was added thereto until the reaction solution became homogenous. The reaction solution was left as it was at room temperature for 45 min. The solvent was evaporated, and then water was added thereto and 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 0.22 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 hydrochloric acid
  5. washwashed with ethyl acetate twice
  6. additionby adding a 8N aqueous solution of sodium hydroxide
  7. additionsubsequently, methanol was added
  8. waitThe reaction solution was left as it
  9. customThe solvent was evaporated
  10. additionwater was added
  11. extractionthe mixture was extracted with ethyl acetate thrice
  12. washAfter washing with brine
  13. dry with materialdrying over magnesium sulfate
  14. customthe solvent was evaporated
  15. customThe resulting residue was purified by NH silica gel column chromatography (ethyl acetate/n-hexane system)

Sources & evidence

ORD record
ord-bcffd917d00240ca8f1fe66aa840abd2
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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