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A preparing process of a compound

A compound and process technology, applied in the field of preparing mirabegron, can solve the problems of difficult purification of condensation products, unfavorable industrial production, difficult raw material sources, etc., and achieves simple and easy-to-obtain splitting reagents, short synthetic process routes, and avoidance of high toxicity. effect of chemicals

Inactive Publication Date: 2015-09-02
HUMANWELL HEALTHCARE GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the current related technology for preparing mirabegron, there are the following problems: the source of raw materials is difficult and expensive, the use of expensive and highly toxic borane, the condensation product is difficult to purify, and the yield is low, so it is not conducive to industrial production. need
[0006] Therefore, the method for preparing Mirabegron still needs to be improved at present

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0036] At room temperature, dissolve epoxystyrene (12g, 0.1mol) and potassium carbonate (20.7g, 0.15mol) in 1,4-dioxane 100ml, then add p-nitrophenylethylamine (16.6g, 0.1mol ), after the addition, heated to 60°C, reacted for 12 hours, filtered, concentrated to remove most of the dioxane, slowly added to 500ml of water, crystallized, filtered, and dried to obtain 24.20g of white solid, which is formula 4 The compound shown has a yield of 84.73%.

[0037] The analysis data is:

[0038] 1 H-NMR (CDCl 3 , 400MHz): δ8.10-8.20(m, 2H), δ7.41-7.24(m, 7H), δ4.70(d, 1H), δ2.80-3.10(m, 5H), δ2.74( d, 1H).

Embodiment 2

[0040] At room temperature, styrene oxide (12g, 0.1mol) and sodium carbonate (15.9g, 0.15mol) were dissolved in 100ml of acetonitrile, then p-nitrophenylethylamine (15.8g, 0.095mol) was added, after the addition was complete , heated to 55°C, reacted for 10 hours, filtered, concentrated to remove most of the acetonitrile, slowly added to 500ml of water, crystallized, filtered, and dried to obtain 21.87g of white solid, which is the compound shown in formula 4, with a yield of 76.58% .

Embodiment 3

[0042] At room temperature, styrene oxide (12g, 0.1mol) and sodium bicarbonate (12.6g, 0.15mol) were dissolved in 100ml of acetone, then p-nitrophenylethylamine (18.26g, 0.11mol) was added, and the addition was complete Afterwards, heated to 65°C, reacted for 13 hours, filtered, concentrated to remove most of the acetone, slowly added to 500ml of water, crystallized, filtered, and dried to obtain 22.49g of white solid, which was the compound shown in Formula 4, with a yield of 78.75 %.

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Abstract

A preparing process of a compound shown as a formula 1 is provided. The process includes (1) bringing a compound shown as a formula 2 into contact with compound shown as a formula 3 to produce a compound shown as a formula 4; (2) subjecting the compound shown as the formula 4 to chiral resolution to produce a compound shown as a formula 5; (3) subjecting the compound shown as the formula 5 to nitro reduction to obtain a compound shown as a formula 6; and (4) bringing the compound shown as the formula 6 into contact with a compound shown as a formula 7 to produce the compound shown as the formula 1. The process is short in route. Initial raw materials are cheap and easily available. All the intermediates are easy to purify and simple in after-treatment. The product is high in purity and high in yield. The process benefits industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and specifically relates to a compound preparation process, more specifically to a preparation process of Mirabegron. Background technique [0002] Mirabegron (i.e. the compound shown in formula 1), the chemical name is (R)-2-(2-amino-1,3-thiazol-4-yl)-4'-[2-[2-(2- Hydroxy-2-phenylethyl)amino]ethyl]phenylacetamide. It was developed by Astellas Corporation of Japan and first launched in Japan in September 2011. It was approved by the US FDA in June 2012 for the treatment of overactive bladder in adults. [0003] [0004] In the related art, EP1440969A discloses that R-hydroxyphenylacetic acid is used as the starting raw material, undergoes condensation, reduction, re-reduction, and finally condenses with 2-amino-4-thiazoleacetic acid to obtain mirabegron. This method utilizes the condensing agent , post-processing is more troublesome, in addition, the use of highly toxic borane is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/40C07C215/30C07C213/04
Inventor 王学海李莉娥许勇乐洋夏庆丰郭涤亮黄璐肖强田华
Owner HUMANWELL HEALTHCARE GRP
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