Hydrochloric Acid → HCID 22502710, compound

HRID 1007044Notes

Reaction equation

HRID 1007044 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]([S:42]([CH2:45][CH2:46][CH3:47])(=[O:44])=[O:43])=[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:48]>C(OCC)(=O)C>[ClH:48].[ClH:48].[CH2:19]([N:21]1[CH2:26][CH2:25][N:24]([C:27]2[N:28]=[C:29]([C:36]3[CH:37]=[CH:38][C:39]([S:42]([CH2:45][CH2:46][CH3:47])(=[O:44])=[O:43])=[CH:40][CH:41]=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 22502711HCID 22502711, compoundHCID 22503093HCID 22503093, compound

Product 1

HCID 22502710HCID 22502710, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The resulting compound and 7-(1-ethylpiperazin-4-yl)-5-bromothieno[2,3-c]pyridine (0.18 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-propanesulfonylphenyl)thieno[2,3-c]pyridine. To the resulting reaction solution were added ethyl acetate and 2N hydrochloric acid, 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. The pH of the solution was adjusted to pH 10 by adding a 8N aqueous sodium hydroxide thereto, and then the solution was extracted with ethyl acetate twice. It was washed with brine, dried over magnesium sulfate, and then the solvent was evaporated. The resulting residue was purified by NH silica gel column chromatography (ethyl acetate/n-hexane system), to give 0.19 g of the free compound of the title compound as a pale brown viscous oil.

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 layer
  5. extractionwas extracted with 2N hydrochloric acid
  6. washwashed with ethyl acetate
  7. additionby adding a 8N aqueous sodium hydroxide
  8. extractionthe solution was extracted with ethyl acetate twice
  9. washIt was washed with brine
  10. dry with materialdried over magnesium sulfate
  11. customthe solvent was evaporated
  12. customThe resulting residue was purified by NH silica gel column chromatography (ethyl acetate/n-hexane system)

Sources & evidence

ORD record
ord-27856a82df4e4f02b76b9ae83f362ae0
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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