Sodium hydride → N-(2-Pyridyl)-1-[2-(4-(3,4-dimethoxybenzoyl)-1-piperazinyl)ethyl]-5,6-dimethoxybenzimidazole-2-carboxamide

HRID 476898Notes

Reaction equation

HRID 476898 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([C:10]1[NH:11][C:12]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[CH:15][C:13]=2[N:14]=1)=[O:9].[H-].[Na+].[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:41]=[CH:42][C:43]=1[O:44][CH3:45])[C:30]([N:32]1[CH2:37][CH2:36][N:35]([CH2:38][CH2:39]Cl)[CH2:34][CH2:33]1)=[O:31]>CS(C)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([C:10]1[N:11]([CH2:39][CH2:38][N:35]2[CH2:36][CH2:37][N:32]([C:30](=[O:31])[C:29]3[CH:41]=[CH:42][C:43]([O:44][CH3:45])=[C:27]([O:26][CH3:25])[CH:28]=3)[CH2:33][CH2:34]2)[C:12]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[CH:15][C:13]=2[N:14]=1)=[O:9]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 118091532-[4-(3,4-Dimethoxybenzoyl)-1-piperazinyl]ethyl chlorideHCID 19837066N-(2-pyridyl)-5,6-dimethoxybenzimidazole-2-carboxamide

Product 1

HCID 14371293N-(2-Pyridyl)-1-[2-(4-(3,4-dimethoxybenzoyl)-1-piperazinyl)ethyl]-5,6-dimethoxybenzimidazole-2-carboxamideYield 44%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

In an argon atmosphere, N-(2-pyridyl)-5,6-dimethoxybenzimidazole-2-carboxamide (0.85 g) was dissolved in DMSO (15 ml), and 60% sodium hydride (0.16 g) was added and stirred at room temperature for 1 hr. A solution (5 ml) of 2-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]ethyl chloride (1.25 g) in DMSO was added dropwise and allowed to react overnight at room temperature under agitation. After-treatment and purification in the same manner as described in Example 14 gave the title compound (0.72 g) as amorphous solid.

Workup

  1. customto react overnight at room temperature under agitation
  2. customAfter-treatment and purification in the same manner

Sources & evidence

ORD record
ord-2f436732b9d94704a5febb0c7011db82
Source dataset
uspto-grants-1989_12
Patent number
US04886803

Reaction notes

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