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Method for preparing 5-(4-((2S, 5S)-5-(4-chlorobenzyl)-2-methylmorpholino) piperidine-1-yl)-1H-1, 2, 4-triazole-3-amine

A technology of methylmorpholine and chlorobenzyl, applied in the preparation of 5-(4-((2S,5S)-5-(4-chlorobenzyl)-2-methylmorpholino)piperidine-1 -base)-1H-1,2,4-triazol-3-amine field, can solve problems such as untaught

Pending Publication Date: 2022-05-10
ONCOARENDI THERAPEUTICS SA
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  • Claims
  • Application Information

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Problems solved by technology

The patent does not teach that simple precipitation of the end product enables the production of a material of strictly defined particle size in a reproducible manner

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  • Method for preparing 5-(4-((2S, 5S)-5-(4-chlorobenzyl)-2-methylmorpholino) piperidine-1-yl)-1H-1, 2, 4-triazole-3-amine
  • Method for preparing 5-(4-((2S, 5S)-5-(4-chlorobenzyl)-2-methylmorpholino) piperidine-1-yl)-1H-1, 2, 4-triazole-3-amine
  • Method for preparing 5-(4-((2S, 5S)-5-(4-chlorobenzyl)-2-methylmorpholino) piperidine-1-yl)-1H-1, 2, 4-triazole-3-amine

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[0014] The present invention provides an efficient and scalable method for the synthesis of (2S,5S)-5-(4-chlorobenzyl)-2-methyl-4-(piperidin-4-yl)morpholine of formula 5 method. Various changes were introduced into the procedure to increase the yield and to simplify the synthesis, making it scalable in comparison to the original method described in the "Background of the Invention". At 0°C to reflux temperature, preferably ambient temperature, make the compound of formula 2 and N-(tert-butoxycarbonyl)-4-piperidone of formula 3 in the presence of sodium cyanoborohydride reducing agent and additive (preferably zinc chloride) in a solvent (preferably alcohol, more preferably methanol). When the starting material is completely converted, tert-butyl 4-((2S,5S)-5-(4-chlorobenzyl)-2-methylmorpholino)piperidine-1-carboxylate of formula 4 is isolated by extraction ester, the crude product is dissolved in a solvent, preferably ethyl acetate, and a solution of hydrochloric acid, prefer...

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Abstract

The invention relates to a method for synthesizing 5-(4-((2S, 5S)-5-(4-chlorobenzyl)-2-methylmorpholino) piperidine-1-yl)-1H-1, 2, 4-triazole-3-amine in two hydrated crystal forms and one anhydrous crystal form. The invention also relates to the methyl (Z)-4-((2S, 5S)-5-(4-chlorobenzyl)-2-methylmorpholino)-N-cyanopiperidine-1-thiomethimides, which are intermediates of this method.

Description

[0001] field of invention [0002] The present invention relates to the synthesis of two hydrated crystal forms and one anhydrous crystal form of 5-(4-((2S,5S)-5-(4-chlorobenzyl)-2-methylmorpholino)piperidine- 1-yl)-1H-1,2,4-triazol-3-amine method. The present invention also relates to (Z)-4-((2S,5S)-5-(4-chlorobenzyl)-2-methylmorpholino)-N-cyanopiperidine-1-thioformimine acid methyl ester, which is an intermediate in this process. [0003] Background of the invention [0004] 5-(4-((2S,5S)-5-(4-chlorobenzyl)-2-methylmorpholino)piperidin-1-yl)-1H-1,2,4-tri Azol-3-amines were first described in International Patent Application WO2017 / 037670. [0005] [0006] The compound of formula 1 is a dual inhibitor of acidic mammalian chitinase (AMCase) and chitotriosidase 1 (CHIT-1). This compound is useful in the treatment of conditions associated with the overexpression of these enzymes. Such conditions are asthma and anaphylaxis or idiopathic pulmonary fibrosis (IPF) and chroni...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/04C07D413/14C07D211/74
CPCC07D413/04C07D413/14C07D211/74C07B2200/13C07B2200/07Y02P20/55A61K31/5377
Inventor G·维特科夫斯基M·马格迪茨M·蒂兹基维茨M·扎克泽夫斯基S·皮库尔
Owner ONCOARENDI THERAPEUTICS SA