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Preparation method of azetidine compound

A compound and catalyst technology, applied in the field of preparation of azetidine compounds, can solve the problems of cumbersome post-processing process, unfavorable industrialization, and many reaction steps, etc.

Pending Publication Date: 2021-01-15
宜昌东阳光制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In the prior art, there are multiple methods for the preparation of baricitinib, and these methods have many reaction steps, long reaction time, or cumbersome operation process and post-treatment process, w

Method used

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  • Preparation method of azetidine compound
  • Preparation method of azetidine compound
  • Preparation method of azetidine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060]Example 1: Preparation of Compound A

[0061]Add toluene (400mL) and potassium tert-butoxide (68.17g, 608mmol) into the reaction flask; control to 0±5℃, add cyanomethyl diethyl phosphate solution (106.58g, 602mmol) dropwise to the system. After the addition, control the temperature to 0±5℃, keep stirring for 0.5h; slowly add N-Boc cyclobutanone solution (100g, 584mmol) dropwise, after the addition, control the temperature at 0±5℃ to react for 2-3h; add to the system It was quenched with water (500 mL), heated to 25±5°C, stirred for 15 min, allowed to stand for layering, and separated; the organic phase was used directly in the next step without treatment; purity by HPLC: 98.7%.

Embodiment 2

[0062]Example 2: Preparation of Compound 01

[0063]At 25°C, add 1,8-diazabicyclo[5.4.0]undec-7-ene (that is, the reaction flask containing compound A (the yield is calculated as 100%) obtained in Example 1) DBU, 88.95g, 585mmol), compound B (115.61g, 596mmol) was heated to 80±5°C and reacted for 2h-3h; the solvent was concentrated under reduced pressure to obtain compound 01 concentrate with a purity of 99.85%, which was directly used in the next reaction.

Embodiment 3

[0064]Example 3: Preparation of Compound 02

[0065]At 25±5℃, add n-butanol (750mL), water (250mL), compound C (39.61g) to a reaction flask containing compound 01 (100g, 258mmol, the concentrate obtained in Example 2 is converted according to the purity data). , 258mmol), NaHCO3(32.45g, 386mmol), tetrakis(triphenylphosphine) palladium (1.49g, 1.29mmol); Replace nitrogen three times, warm up to 85±2℃, keep stirring for 15h-16h; after the reaction is over, the reaction solution is directly without post-treatment For the next step, the reaction solution was tested, and the purity of the product was 98.78%.

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Abstract

The invention relates to a preparation method of an azetidine compound, belonging to the field of medicinal chemistry. The preparation method comprises the following step: carrying out multi-step reactions on raw materials to obtain the azetidine compound or a salt thereof, wherein an intermediate is not separated. The azetidine compound or the salt thereof reacts with ethanesulfonyl chloride to obtain a final target drug. According to the preparation method provided by the invention, in the preparation process, multi-step reactions are connected in series, and a part of the intermediates is not separated; and the process is simple, convenient, smooth and continuous, a preparation period is short, and industrial implementation is facilitated.

Description

Technical field[0001]The invention relates to the field of medicinal chemistry, in particular to a method for preparing an azetidine compound.Background technique[0002]Baritinib, the English name baricitinib, is a drug used to treat rheumatoid arthritis. Its structure is as follows:[0003][0004]In the prior art, there are many methods for the preparation of baritinib. These methods have many reaction steps, long reaction time, or complicated operation and post-treatment processes, which are not conducive to industrialization; therefore, it is still necessary to study its Preparation method in order to obtain a simpler method that is easy to implement on a large scale in industry.Summary of the invention[0005]In order to obtain baritinib more simply, according to one aspect of the present invention, the present invention provides a method for preparing an intermediate azetidine for preparing baritinib. In order to simplify the process, make the process smoother, continuous, and have a...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 雷鑫周有柏王仲清陈伟贵李春明罗忠华黄芳芳
Owner 宜昌东阳光制药有限公司
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