Chloroform → 2-[4-[2-(benzimidazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acetamide dimaleate

HRID 1064862Notes

Reaction equation

HRID 1064862 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[S:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]([NH:22][C:23]2[C:24]([S:32][CH3:33])=[N:25][C:26]([CH3:31])=[CH:27][C:28]=2[S:29][CH3:30])=[O:21])[CH2:15][CH2:14]1.[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]\[C:37]([OH:39])=[O:38].C(Cl)(Cl)Cl>C(O)C>[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]\[C:37]([OH:39])=[O:38].[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]\[C:37]([OH:39])=[O:38].[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[S:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][N:16]([CH2:19][C:20]([NH:22][C:23]2[C:24]([S:32][CH3:33])=[N:25][C:26]([CH3:31])=[CH:27][C:28]=2[S:29][CH3:30])=[O:21])[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 444266Maleic AcidHCID 9892288K-604

Product 1

HCID 865912422-[4-[2-(benzimidazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acetamide dimaleateYield 78.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-[4-[2-(benzimidazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acetamide (4.58 g, 9.11 mmol) obtained in Example 32 in ethanol (170 ml) was added maleic acid (2.11 g, 18.2 mmol) with ice-cooling. The mixture was homogenized by adding chloroform (20 ml) and concentrated in vacuo. The resulting reside was crystallized from ethanol-ether to provide 5.27 g (yield 77%) of 2-[4-[2-(benzimidazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acetamide dimaleate.

Workup

  1. temperaturecooling
  2. concentrationconcentrated in vacuo
  3. customThe resulting reside was crystallized from ethanol-ether

Sources & evidence

ORD record
ord-b9dcdec315a4449db5a7970707f58c00
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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