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Method for preparing 4-methyl-2-propyl-1H-benzimidazole-6-formamide compound

A technology of amine compounds and benzimidazole, which is applied in the field of chemical synthesis, can solve the problems of low product purity, large environmental pollution, and low reaction yield, and achieve the effects of good purity, low environmental pollution, and high product yield

Inactive Publication Date: 2010-07-21
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The purpose of the present invention is to provide a kind of 4-methyl-2-propyl- The preparation method of 1H-benzimidazole-6-carboxamides

Method used

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  • Method for preparing 4-methyl-2-propyl-1H-benzimidazole-6-formamide compound
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  • Method for preparing 4-methyl-2-propyl-1H-benzimidazole-6-formamide compound

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Example 1 Preparation of 4-methyl-2-propyl-N-propyl-1H-benzimidazole-6-carboxamide

[0027] Add 5.0g (23mmol) of 4-methyl-2-propyl-1H-benzimidazole-6-carboxylic acid and 20mL of N,N-dimethylformamide into a 500mL three-necked flask, and add N,N'- Carbonyldiimidazole 3.7g (23mmol), stirred at room temperature for 30min, then added n-propylamine 1.3g (23mmol), continued to stir at 100°C for 4h after the addition, evaporated the solvent under reduced pressure, added water to the residue and stirred until the solid precipitated completely. Suction filtration and drying yielded 5.9 g, yield 94%. 1 H NMR (DMSO-d 6 , 400MHz) δ: 0.91(t, J=7.25Hz, 3H), 0.95(t, J=7.24Hz, 3H), 1.59(m, 2H), 1.76(m, 2H), 2.55(s, 3H), 2.78(t, J=7.24Hz, 2H), 3.21(m, 2H), 7.47(s, 1H), 7.81(s, 1H).

Embodiment 2

[0028] Example 2 Preparation of 4-methyl-2-propyl-N-propyl-1H-benzimidazole-6-carboxamide

[0029] Add 5.0 g (23 mmol) of 4-methyl-2-propyl-1H-benzimidazole-6-carboxylic acid into a 500 mL three-necked flask, 30 mL of dichloromethane, and add N, N'-carbonyldiimidazole 3.7 g ( 23mmol), stirred at room temperature for 30min, then added 1.3g (23mmol) of propylamine, continued to stir at room temperature for 12h after the addition, and evaporated the solvent. Add water to the residue and stir until the solid precipitates out completely. Suction filtration and drying yielded 5.5 g with a yield of 93%. 1 H NMR (DMSO-d 6 , 400MHz) δ: 0.91(t, J=7.25Hz, 3H), 0.95(t, J=7.24Hz, 3H), 1.59(m, 2H), 1.76(m, 2H), 2.55(s, 3H), 2.78(t, J=7.24Hz, 2H), 3.21(m, 2H), 7.47(s, 1H), 7.81(s, 1H).

Embodiment 34

[0030] Preparation of Example 34-methyl-2-propyl-N-isopropyl-1H-benzimidazole-6-carboxamide

[0031] The amine compound uses 23mmol isopropylamine, and other feeding and implementation methods are the same as in Example 2. 5.4 g of white solid was obtained with a yield of 91%. 1 H NMR (DMSO-d 6 , 400MHz) δ: 0.94(t, J=7.21Hz, 3H), 1.25(d, J=7.22Hz, 6H), 1.76(m, 2H), 2.55(s, 3H), 2.79(t, J=7.24 Hz, 2H), 3.94 (m, 1H), 7.46 (s, 1H), 7.83 (s, 1H).

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Abstract

The invention relates to a method for preparing a 4-methyl-2-propyl-1H-benzimidazole-6-formamide compound, belonging to the field of chemical synthesis. The method is characterized by utilizing N,N'-carbonyldiimidazole to activate 4-methyl-2-propyl-1H-benzimidazole-6-formic acid, and then carrying out amidation reaction to obtain the target product. The synthetic route is as follows. The method is low in cost, short in synthetic route, simple and convenient to operate, high in product yield, good in purity, low in environmental pollution and beneficial to industrialized production.

Description

technical field [0001] The invention relates to a preparation method of 4-methyl-2-propyl-1H-benzimidazole-6-carboxamide compounds, belonging to the field of chemical synthesis. Background technique [0002] Angiotensin II (AngII) AT 1 Receptor antagonists are widely used in the treatment of hypertension. Losartan is a typical AngII AT 1 receptor antagonist, numerous structural modifications based on losartan have produced multiple AngII AT 1 Receptor antagonists, such as candesartan, irbesartan, telmisartan, etc. [0003] Chinese patent CN100506799C uses losartan as the lead compound for structural modification and transformation, and designs and synthesizes [(4-methyl-2-propyl-1H-benzimidazole-6-carboxamide)-1-yl with novel chemical structure ] methyl biphenyl compound, wherein the key intermediate is 4-methyl-2-propyl-1H-benzimidazole-6-carboxamide compound (I), [0004] [0005] where R 1 Represents β-phenethyl or (4-methylpiperazin-1-yl)ethyl. [0006] Literat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/08
Inventor 周智明汪进良章军薛为哲何星李志怀
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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