Bromide ion → HCID 22709662, compound

HRID 1061033Notes

Reaction equation

HRID 1061033 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:21][CH2:20][N:19]([C:22]([C:24]3[S:32][C:31]4[CH2:30][CH2:29][NH:28][CH2:27][C:26]=4[CH:25]=3)=[O:23])[CH2:18][CH2:17]1)(=[O:15])=[O:14])[CH:7]=[CH:6]2.[CH2:33]([N:35](CC)CC)C.C([O-])(=O)C.[Na+].[Br-]>C(O)C>[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:17][CH2:18][N:19]([C:22]([C:24]3[S:32][C:31]4[CH2:30][CH2:29][N:28]([C:33]#[N:35])[CH2:27][C:26]=4[CH:25]=3)=[O:23])[CH2:20][CH2:21]1)(=[O:15])=[O:14])[CH:7]=[CH:6]2

Participants

6

Reactant 4

HCID 259Bromide ionHCID 8471TriethylamineHCID 517045Sodium AcetateHCID 11398144HCID 11398144, compound

Product 1

HCID 22709662HCID 22709662, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol, 1-[(6-chloronaphthalen-2-yl)sulfonyl]-4-[(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)carbonyl]piperazine hydrochloride (195 mg), triethylamine (0.2 ml) and sodium acetate (118 mg) were suspended, followed by the addition of cyan bromide (114 mg). The resulting mixture was stirred at room temperature for 2 hours. The residue obtained by concentrating the reaction mixture under reduced pressure was added with dichloromethane, followed by washing with water. After drying over anhydrous sodium sulfate, the residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (dichloromethane:methanol=100:1), whereby the title compound (51 mg, 28%) was obtained.

Workup

  1. customThe residue obtained
  2. concentrationby concentrating the reaction mixture under reduced pressure
  3. additionwas added with dichloromethane
  4. washby washing with water
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. customthe residue obtained
  7. distillationby distilling off the solvent under reduced pressure
  8. customwas purified by chromatography on a silica gel column (dichloromethane:methanol=100:1), whereby the title compound (51 mg, 28%)
  9. customwas obtained

Sources & evidence

ORD record
ord-141902c71e484d4ab1b6e2ec954e898c
Source dataset
uspto-grants-2003_02
Patent number
US06525042B1

Reaction notes

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