2-Amino-4,6-dimethylpyridine → N-(4,6-dimethyl-2-pyridyl)-1-(N,N-dimethylsulfamoyl)-5,6-dimethoxybenzimidazole-2-carboxamide

HRID 476895Notes

Reaction equation

HRID 476895 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[H-].[Na+].[CH3:12][N:13]([CH3:35])[S:14]([N:17]1[C:21]2[CH:22]=[C:23]([O:28][CH3:29])[C:24]([O:26][CH3:27])=[CH:25][C:20]=2[N:19]=[C:18]1[C:30](OCC)=[O:31])(=[O:16])=[O:15].[Cl-].[NH4+]>CS(C)=O>[CH3:8][C:6]1[CH:5]=[C:4]([CH3:9])[N:3]=[C:2]([NH:1][C:30]([C:18]2[N:17]([S:14](=[O:16])(=[O:15])[N:13]([CH3:35])[CH3:12])[C:21]3[CH:22]=[C:23]([O:28][CH3:29])[C:24]([O:26][CH3:27])=[CH:25][C:20]=3[N:19]=2)=[O:31])[CH:7]=1

Participants

6

Reactant 4

HCID 215072-Amino-4,6-dimethylpyridineHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 143712791-(N,N-dimethylsulfamoyl)-2-ethoxycarbonyl-5,6-dimethoxybenzimidazole

Product 1

HCID 19837071N-(4,6-dimethyl-2-pyridyl)-1-(N,N-dimethylsulfamoyl)-5,6-dimethoxybenzimidazole-2-carboxamideYield 67.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

In a dry argon atmosphere, 2-amino-4,6-dimethyl pyridine (4.0 g) was dissolved in dry DMSO (30 ml), 60% sodium hydride (1.30 g) was added and stirred at room temperature for 1 hr. A solution of 1-(N,N-dimethylsulfamoyl)-2-ethoxycarbonyl-5,6-dimethoxybenzimidazole (6.56 g) in DMSO (15 ml) was added dropwise while cooling and stirred at room temperature for 2 hrs. The reaction solution was poured into aqueous saturated ammonium chloride solution and extracted with benzene. The residue obtained by distilling off the solvent was purified by column chromatography on silica gel to obtain N-(4,6-dimethyl-2-pyridyl)-1-(N,N-dimethylsulfamoyl)-5,6-dimethoxybenzimidazole-2-carboxamide (5.40 g). This compound was dissolved in THF (250 ml), and then water (70 ml) and conc. hydrochloric acid (7 ml) were added allowed to react overnight at room temperature under agitation. The reaction solution was neutralized with ammonia water, THF was distilled off and the precipitated crystals were filtered off. The crystals obtained was recrystallized from chloroform/methanol to give the title compound (3.45 g).

Workup

  1. temperaturewhile cooling
  2. stirringstirred at room temperature for 2 hrs
  3. extractionextracted with benzene
  4. customThe residue obtained
  5. distillationby distilling off the solvent
  6. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-72fd3f00422f46fc95812279082e5225
Source dataset
uspto-grants-1989_12
Patent number
US04886803

Reaction notes

Loading…