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

HRID 2354010Notes

Reaction equation

HRID 2354010 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(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

4

Reactant 2

HCID 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 89.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The free base (23.75 g, 47.2 mmol) of 2-[4-[2-(benzimidazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acetamide was dissolved in ethanol (200 mL). Maleic acid (11.4 g, 98.2 mol) was added and dissolved under heat to prepare a homogeneous solution. The reaction mixture was concentrated under reduced pressure and the residue was crystallized from ethanol-ethyl acetate. The crystals were collected by filtration to afford the title compound (30.95 g, 89.1%) as colorless crystals.

Workup

  1. dissolutiondissolved
  2. temperatureunder heat
  3. customto prepare a homogeneous solution
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customthe residue was crystallized from ethanol-ethyl acetate
  6. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-895f9766fa194f3b8f0572673f17d798
Source dataset
uspto-grants-2010_07
Patent number
US07750150B2

Reaction notes

Loading…