Baricitinib intermediate and preparation method thereof and method for preparing baricitinib from the intermediate

A baricitinib and intermediate technology, applied in the field of small molecule drug preparation, can solve the problems of limited industrial production of compounds, complex by-products, numerous reaction routes, etc., and achieves good market application prospects, high product purity, and simple process steps. Effect
CN105541891BActive Publication Date: 2017-11-28SOUTHEAST UNIV
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Patent Information

Authority / Receiving Office
CN · China
Current Assignee / Owner
SOUTHEAST UNIV
Publication Date
2017-11-28

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Abstract

The invention discloses a baricitinib intermediate and a preparation method thereof, and a method for preparing baricitinib from the intermediate. The structure of the intermediate is disclosed as Formula (5). The preparation method of the intermediate comprises the following steps: carrying out reaction on diethyl cyanomethylphosphate and 1-boc-3-azacyclobutanone under the catalytic action of an alkali to obtain a compound 2 disclosed as Formula (2); removing the Boc group of the compound 2 to obtain a compound 3 disclosed as Formula (3); under alkaline conditions, carrying out reaction on the compound 3 and ethyl sulfonyl chloride to obtain a compound 4 disclosed as Formula (4); and in the presence of 1,8-diazabicyclo[5,4,0]hendecyne-7-ene, carrying out reaction on the compound 4 and pinacone 4-pyrazolylborate to obtain the intermediate. The method for preparing baricitinib from the intermediate comprises the following step: in the presence of a palladium catalyst and cesium fluoride, carrying out Suzuki coupling reaction on the intermediate and 6-chloro-7-deazapurine to obtain the baricitinib. The preparation method of baricitinib has the advantages of accessible raw materials and simple technique, and is suitable for industrial production.
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Description

technical field

[0001] The invention relates to the preparation of small molecule drugs, in particular to an intermediate of pyrrolopyrimidine JAK inhibitor drug baricitinib, a preparation method thereof and a method for preparing baricitinib from the intermediate. Background technique

[0002] Rheumatoid arthritis (RA) is an autoimmune disease characterized by persistent synovitis and progressive bone destruction in multiple joints, the pathogenesis of which has not yet been fully understood. Studies have shown that immune disorders in RA patients are mainly mediated by TNF-α, IL-1, IL-6 and other cytokines, which are activated through specific signaling pathways to exert their biological effects. JAK-STAT signaling pathway (Janus-activited kinase-signal transducer and cativator of transcriptions, JAK-STAT) is one of the important signal transduction pathways, which is widely involved in regulating the pathophysiological process of diseases, especially playing an important ...

Claims

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