Sodium hydride → N-Methyl-N-(4,6-dimethyl-2-pyridyl)-1-[2-(4-(3,4-dimethoxybenzoyl)-1-piperazinyl)ethyl]benzimidazole-2-carboxamide

HRID 476896

Reaktionsgleichung

Reaktionsgleichung von HRID 476896
[CH3:1][N:2]([C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[N:15]=1)[C:3]([C:5]1[NH:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)=[O:4].[H-].[Na+].[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:40]=[CH:41][C:42]=1[O:43][CH3:44])[C:29]([N:31]1[CH2:36][CH2:35][N:34]([CH2:37][CH2:38]Cl)[CH2:33][CH2:32]1)=[O:30].[Cl-].[NH4+]>CS(C)=O>[CH3:1][N:2]([C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[N:15]=1)[C:3]([C:5]1[N:6]([CH2:38][CH2:37][N:34]2[CH2:35][CH2:36][N:31]([C:29](=[O:30])[C:28]3[CH:40]=[CH:41][C:42]([O:43][CH3:44])=[C:26]([O:25][CH3:24])[CH:27]=3)[CH2:32][CH2:33]2)[C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)=[O:4]

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 118091532-[4-(3,4-Dimethoxybenzoyl)-1-piperazinyl]ethyl chlorideHCID 14371319N-methyl-N-(4,6-dimethyl-2-pyridyl)benzimidazole-2-carboxamide

Produkt 1

HCID 9809995N-Methyl-N-(4,6-dimethyl-2-pyridyl)-1-[2-(4-(3,4-dimethoxybenzoyl)-1-piperazinyl)ethyl]benzimidazole-2-carboxamideAusbeute 79,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Versuchsvorschrift

In an argon atmosphere, N-methyl-N-(4,6-dimethyl-2-pyridyl)benzimidazole-2-carboxamide (2.00 g) was dissolved in DMSO (15 ml), and 60% sodium hydride (0.33 g) was added and stirred at room temperature for 1 hr. A solution (7 ml) of 2-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]ethyl chloride (2.20 g) in DMSO was added dropwise and allowed to react overnight at room temperature under agitation. The reaction solution was added to an aqueous solution of ammonium chloride and extracted with chloroform, the chloroform layer was dried over Na2SO4, and the solvent was distilled off. Purification of the residue by column chromatography gave the title compound (3.10 g) as amorphous solid.

Aufarbeitung

  1. customto react overnight at room temperature under agitation
  2. extractionextracted with chloroform
  3. dry with materialthe chloroform layer was dried over Na2SO4
  4. distillationthe solvent was distilled off
  5. customPurification of the residue by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f6323285af62467588d63c16ce98f4cc
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04886803

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