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A kind of synthetic method of jak1 inhibitor filgotinib

A compound and catalyst technology, applied in the field of synthesis of JAK1 inhibitor Filgotinib, can solve the problem of ineffective correction of rheumatoid arthritis and osteoarthritis diseases

Active Publication Date: 2022-05-20
四川伊诺达博医药科技有限公司
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are currently no effective drugs for the correction of rheumatoid arthritis and osteoarthritis disease

Method used

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  • A kind of synthetic method of jak1 inhibitor filgotinib
  • A kind of synthetic method of jak1 inhibitor filgotinib

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Experimental program
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Embodiment 1

[0062] Embodiment 1, the synthesis of compound Filgotinib

[0063] According to the following synthetic route, compound Filgotinib is prepared:

[0064]

[0065] 1, Synthesis of 6-(4-methylphenyl)-2-aminopyridine (compound 1)

[0066] Add 2-amino-6-bromopyridine (50g, 0.29mol), p-tolylboronic acid (47g, 0.35mol), 1,4-dioxane (750ml) and water (250ml) into the reaction flask, Potassium acetate (85 g, 0.87 mol) and [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (Pd(dppf)Cl) were added 2 , 12.7g, 0.0174mol). Nitrogen was introduced, heated to reflux for 13 hours, and the reaction was monitored by TLC. Cool down to room temperature, add 2N hydrochloric acid to PH>3, precipitate solid, filter, dissolve the filter cake with 2N aqueous sodium hydroxide solution, extract with ethyl acetate (300mlX3), concentrate the organic phase to obtain the product 6-(4-methylphenyl )-2-aminopyridine (compound 1) 144.7g, yield 83.6%.

[0067] 2. Synthesis of [6-(4-methylphenyl)p...

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Abstract

The invention provides a preparation method of Filgotinib, comprising the following steps: (1) reacting 2-amino-6-bromopyridine with p-toluene derivatives to prepare compound 1; (2) compound 1 and isothiocyanate formic acid Ethyl reaction to prepare compound 2; (3) compound 2 reacted with hydroxylamine hydrochloride and N,N-diisopropylethylamine to prepare compound 3; (4) compound 3 reacted with cyclopropanoyl chloride to obtain compound 4; ( 5) Compound 4, N-bromosuccinimide was reacted with azobisisobutyronitrile to obtain compound 5; (6) Compound 5 was reacted with thiomorpholine-1,1-dioxide to obtain Filgotinib. The route for synthesizing Filgotinib in the present invention is coupling first and then ring closing, the raw materials are cheap, the reaction operation is simple, the product is easy to purify, and the yield is high, which is suitable for commercial scale production.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a method for synthesizing JAK1 inhibitor Filgotinib. Background technique [0002] Cartilage degeneration is a hallmark of many diseases, of which rheumatoid arthritis and osteoarthritis are the most important. Rheumatoid arthritis (RA) is a chronic joint degenerative disease characterized by inflammation and destruction of joint structures. When the disease is unchecked, loss of joint functionality results in substantial disability and pain, and even premature death. However, there are currently no effective drugs for correcting rheumatoid arthritis and osteoarthritic diseases. [0003] Janus kinases (JAKs) are cytoplasmic tyrosine kinases that transduce cytokine signals from membrane receptors to STAT transcription factors. Four JAK family members have been described in the prior art: JAK1, JAK2, JAK3 and TYK2. When cytokines bind to their receptors, JAK family members autopho...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 万华斯涛周平吴夏霍欢徐国燕岳利剑
Owner 四川伊诺达博医药科技有限公司
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