Hydrochloric Acid → HCID 22502842, compound

HRID 1814597Notes

Reaction equation

HRID 1814597 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 soluton 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 soluton 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-33ba3d9e47bb4c2fa8e6b2c6be4d367c
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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