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A kind of synthetic method of Relugoli

A purification method and compound technology, applied in the direction of organic chemistry, can solve the problems of harsh reaction conditions and high equipment requirements

Active Publication Date: 2021-05-28
四川伊诺达博医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this method adopts the method of coupling first and then closing the ring, the reaction conditions are harsh, and the reaction needs to be carried out under heating and pressurized conditions, and the requirements for equipment are relatively high.

Method used

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  • A kind of synthetic method of Relugoli
  • A kind of synthetic method of Relugoli
  • A kind of synthetic method of Relugoli

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] The synthesis of embodiment 1 Relugoli

[0060] According to the following synthetic route, the compound Relugoli was prepared:

[0061]

[0062]

[0063] Synthesis of step 1, ethyl 2-amino-4-methyl-5-(4-nitrophenyl)-3-thiophenecarboxylate (compound 1):

[0064] 4-Nitropropiophenone (30g, 0.17mol), ethyl cyanoacetate (19.2g, 0.17mol) and ethanol (200ml) were added to the reaction flask, stirred and dissolved, then triethylamine (17.2g, 0.17mol ) and sulfur powder (5.4g, 0.17mol), heated to 50°C for 6h, and the reaction was complete by TLC monitoring. Concentrate to remove ethanol, add 300ml of ethyl acetate to the residue, extract with 100ml of saturated brine, and concentrate the organic phase to obtain a crude product. Then crystallize and purify with ethyl acetate / n-hexane (200ml / 200ml), filter, and dry to obtain ethyl 2-amino-4-methyl-5-(4-nitrophenyl)-3-thiophenecarboxylate (compound 1) 35.4g, yield 69%.

[0065] Synthesis of step 2, 2-amino-4-methyl-5-(4...

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Abstract

The present invention provides a method for preparing relugoli intermediate compound 8, said method comprising the following steps: (a) reacting compound 2 with N,N'-carbonyldiimidazole to obtain compound 3; (b) compound 3 React with 2,6-difluorobenzyl chloride to give compound 4; (c) react compound 4 with 3-amino-6-methoxypyridazine to give compound 5; (d) react compound 5 with N,N'-carbonyl Diimidazole reacts to obtain compound 6; (e) compound 6 reacts with N-bromosuccinimide and azobisisobutyronitrile to obtain compound 7; (f) compound 7 reacts with dimethylamine hydrochloride, Compound 8 was obtained. The present invention also provides a method for preparing relugoli, said method comprising the following steps: (g) reacting compound 8 prepared by the above method with hydrogen under a catalyst to obtain compound 9; (h) compound 9 and N , N'‑carbonyldiimidazole and methoxylamine hydrochloride were reacted to obtain relugoli. The method for preparing relugoli provided by the present invention adopts the route of first ring closure and then coupling, which has simpler operation, fewer side reactions, mild reaction conditions, high yield and purity, easy purification of the product, and is suitable for commercial scale production.

Description

technical field [0001] The present invention relates to the field of drug synthesis, in particular to a method for synthesizing relugoli. Background technique [0002] The secretion of anterior pituitary hormones is feedback-controlled by peripheral hormones secreted from various hormone target organs and by secretory-regulatory hormones from the hypothalamus. Currently, nine hormones belonging to the above have been discovered, for example, thyrotropin-releasing hormone (TRH) and gonadotropin-releasing hormone [GnRH, sometimes referred to as LH-RH (luteinizing hormone-releasing hormone)]. The secretion of these hormones is related to their corresponding receptors. Therefore, finding antagonists or agonists that can specifically and selectively act on the receptors can realize the secretion of specific anterior pituitary hormones. [0003] Relugolix, CAS No. 737789-87-6, chemical name N-(4-(1-(2,6-difluorobenzyl)-5-((dimethylamino)methyl) -3-(6-methoxy-3-pyridazinyl)-2,4-d...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04
CPCC07D495/04
Inventor 万华斯涛周平吴夏徐国燕岳利剑
Owner 四川伊诺达博医药科技有限公司
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