Hydrochloric Acid → HCID 22502842, compound

HRID 1251278Notes

Reaction equation

HRID 1251278 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][CH2:44][CH2:45][O:46]C4CCCCO4)=[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(OCC)(=O)C>[ClH:53].[ClH:53].[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][CH2:44][CH2:45][OH:46])=[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 22503622HCID 22503622, compound

Product 1

HCID 22502842HCID 22502842, 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-[3-(tetrahydropyran-2-yl)oxypropoxy]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 thrice. The pH of the resulting solution was adjusted to pH 10 by adding a 8N aqueous solution of sodium hydroxide thereto, and the resulting solution was extracted with ethyl acetate thrice. The extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by NH silica gel column chromatography (ethyl acetate/n-hexane system), to give 0.26 g of the free compound of the title compound as a colorless amorphous.

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 thrice
  6. additionby adding a 8N aqueous solution of sodium hydroxide
  7. extractionthe resulting solution was extracted with ethyl acetate thrice
  8. washThe extract was washed with brine
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent was evaporated
  11. customthe resulting residue was purified by NH silica gel column chromatography (ethyl acetate/n-hexane system)

Sources & evidence

ORD record
ord-5a473c10e43443ad9cff6a528151544e
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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