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

HRID 476895노트

반응식

HRID 476895 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-72fd3f00422f46fc95812279082e5225
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04886803

반응 노트

불러오는 중…