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New method for combining ethyl sulfonamide

A technology of ethanesulfonamide and tert-butoxycarbonylmethanesulfonamide, applied in the synthesis of N-methyl-1H-indole-5-ethanesulfonamide, synthesis of ethanesulfonamide, synthesis of N-methyl-1H-indole - The field of 5-ethanesulfonamide compounds can solve the problems of short steps, cheap and easy-to-obtain raw materials, etc., and achieve the effect of short steps, cheap and easy-to-get raw materials, and less side reactions

Active Publication Date: 2012-05-30
常州市勇毅生物药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, no preparation technology or route can fully meet the industrialization and commercialization requirements of cheap and easy-to-obtain raw materials, short steps, high yield, convenient operation, and environmental friendliness, and further improvement is needed

Method used

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  • New method for combining ethyl sulfonamide
  • New method for combining ethyl sulfonamide
  • New method for combining ethyl sulfonamide

Examples

Experimental program
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Effect test

Embodiment 1

[0048] 1. Synthesis of N-benzyl indoline (5)

[0049] In a 250ml four-necked flask equipped with a dropping funnel and a thermometer, add indoline (4) (50g, 0.42mol), K 2 CO 3 (70g, 0.51mol) and DMF (120ml), stirred and warmed to 100°C. Benzyl bromide (75.42 g, 0.44 mol) was slowly added dropwise over 1 hour. After the dropwise addition was completed, the reaction was incubated for 3 hours, and TLC showed that the reaction was complete. The reaction solution was cooled to room temperature, poured into 1000ml of water, stirred for 0.5 hours, and then separated into layers, and the black oily substance in the lower layer was separated. After stirring and standing, solids would precipitate out, and recrystallized from ethyl acetate to obtain 80.12 g of compound (5), with a yield of 91.3%.

[0050] 2. Synthesis of N-benzyl-5-formaldehyde indoline (6)

[0051] In a 100ml four-necked flask equipped with a dropping funnel and a thermometer, add DMF (20ml), cool the system to bel...

Embodiment 2

[0070] Except for changing the synthesis conditions of compound (11), other steps were the same as in Example 1.

[0071] 1. Synthesis of N-methyl-1H-indoline-5-ethanesulfonamide (11)

[0072] Add compound (9) N-methyl-1H-indoline-5-ethylene sulfonamide (10.0g, 0.042mol) and ethanol 300ml in the hydrogenation kettle, add the Pd / C catalyst that the weight percent of Pd is 10% (5.0g), adjust the hydrogen pressure to 0.5MP, stir and hydrogenate at room temperature for 10 hours. The reaction ends when the hydrogen uptake stops. The Pd / C catalyst was recovered by filtration. The organic solvent in the filtrate was evaporated under reduced pressure, and 8.2 g of compound (11) N-methyl-1H-indoline-5-ethanesulfonamide was obtained by recrystallization, with a yield of 81.3%.

[0073] 2. Synthesis of N-methyl-1H-indoline-5-ethanesulfonamide (11)

[0074] Add compound (8) N-methyl-1-benzyl-indoline-5-ethylenesulfonamide (38.2g, 0.10mol) and THF 500ml in the hydrogenation kettle, and...

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Abstract

The invention belongs to the field of pharmaceutical chemicals and discloses a new method for combining ethyl sulfonamide; in the invention, indoline is used as starting material, and the target compound: N-methyl-1H-benzpyrole-5-ethyl sulfonamide is obtained by the steps of benzyl protection, formylate, condensation with N-methyl methanesulfonamide, hydrogenation reduction, debenzyl and oxidation and the like; in the combining route, the raw material is easily to obtain, the process is simple, the yield is high, the operation is convenient, the environment is friendly, the disadvantages thatthe raw material preparation is difficult and the regent cost is overhigh in the prior art are overcome, and the method has industrial application value.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and relates to a new method for synthesizing ethanesulfonamide, in particular to a method for synthesizing N-methyl-1H-indole-5-ethanesulfonamide and the method for synthesizing N-methyl-1H - Compounds of indole-5-ethanesulfonamide. Background technique [0002] Naratriptan is a second-generation triptan anti-migraine drug developed by Glaxo Wellcome, which has obvious curative effect. Its chemical name is N-methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide (3), and its synthetic method is disclosed in the patent GB2208646 for the first time (corresponding to Patents EP303507 and US4997841). [0003] [0004] The published information shows that there are nine synthetic routes of naratriptan in two categories. One of the major categories is the synthesis of benzene ring-substituted ethanesulfonamide derivatives, followed by indole ring closure and condensation wit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/08
Inventor 曹文一熊小江刘一龙谷道晨周刘斌
Owner 常州市勇毅生物药业有限公司
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