Triethylamine → HCID 22709662, compound

HRID 352848Notes

Reaction equation

HRID 352848 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+].N#CBr>C(O)C.ClCCl>[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

7

Reactant 4

HCID 8471TriethylamineHCID 10476Cyanogen BromideHCID 517045Sodium AcetateHCID 11398144HCID 11398144, compound

Product 1

HCID 22709662HCID 22709662, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

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. Cyanogen bromide (114 mg) was added to the resulting suspension, followed by stirring at room temperature for 2 hours. To the residue obtained by concentration of the reaction mixture under reduced pressure, dichloromethane was added. The mixture was washed with water and dried 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. additionwas added
  2. washThe mixture was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe residue obtained
  5. distillationby distilling off the solvent under reduced pressure
  6. customwas purified by chromatography on a silica gel column (dichloromethane:methanol 100:1), whereby the title compound (51 mg, 28%)
  7. customwas obtained

Sources & evidence

ORD record
ord-46287ccb5f59481baaf055bcbc490655
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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