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Synthesis method of atavapam

A synthesis method and technology of synthesis route, applied in directions such as organic chemistry, can solve the problems of lengthy preparation steps, low yield of final product, etc., and achieve the effects of high ee value, high product yield and obvious industrial practicability.

Pending Publication Date: 2022-04-01
CHONGQING MEDICAL UNIVERSITY
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Problems solved by technology

[0006] This method not only has lengthy preparation steps, but also needs to use ditoluoyl-L-tartaric acid for resolution, and the yield of the final product is low

Method used

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  • Synthesis method of atavapam
  • Synthesis method of atavapam
  • Synthesis method of atavapam

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Experimental program
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Embodiment

[0037] Reaction route:

[0038]

[0039] Steps:

[0040] Dissolve 4.9g (22mmol) of compound 2 with 100mL of anhydrous acetone, add 4.2g (30mmol) of K 2 CO 3 , then added 10 mL of DMF solution containing 5.5 g (20 mmol) of compound 1, stirred and reacted at room temperature for 36 hours, then added 5 g of anhydrous Na 2 SO 4, continued to stir and react at 50° C. for 3 hours, and TLC showed that the reaction was complete. The reaction solution was concentrated under reduced pressure, the residue was dissolved in 200 mL ethyl acetate, washed with saturated NaCl (100 mL X 2) aqueous solution, extracted, and the organic layer was washed with anhydrous NaCl 2 SO 4 It was dried, then concentrated by filtration, and the crude product was separated through a silica gel column. The column solvent was ethyl acetate / petroleum ether=1 / 10 to obtain 6.3 g of compound 3 as a yellow solid with a yield of 72%.

[0041] H1 NMR (400MHz, CDCl3): δ (ppm): 8.38 (d, J = 8.7Hz, 2H), 8.01 (d,...

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Abstract

According to the synthesis method of the atavapam, the atavapam is prepared through the steps of ring closing, chiral reduction, cyclopentanone coupling, 4-methyl-3-(trifluoromethyl) aniline coupling and the like, chiral resolution is avoided in the preparation process, and the yield of the final product is increased. According to the preparation method, bis (1, 5-cyclooctadiene) rhodium tetrafluoroborate (I) (Rh (COD) 2BF4 is used as a catalyst, (R)-Ligand 1 is used as a ligand of the catalyst, specific process parameters are combined to prepare the compound 4, the product yield is high, and the ee value is high. According to the method disclosed by the invention, the atavapam is obtained through four-step reaction, the yield of a final product can reach 42.55%, and the method has obvious industrial practicability.

Description

technical field [0001] The invention relates to avacopam, in particular to a method for synthesizing avacopam. Background technique [0002] Antineutrophil cytoplasmic antibodies (ANCA) are a group of IgG-type autoantibodies that react with the cytoplasm of both neutrophils and monocytes. Interactions between activated neutrophils and ANCA release factors that activate the alternative complement pathway, inducing an amplification loop that is thought to sustain necroinflammation during ANCA-associated vasculitis (AAV) episodes. Alvacopam is an anti-neutrophil cytoplasmic autoantibody (ANCA)-associated vasculitis drug developed by Chemocentrix Inc. of the United States. [0003] WO2016 / 053890 discloses the preparation method of alvacopam, the route is as follows: [0004] [0005] [0006] This method not only has lengthy preparation steps, but also needs to use ditoluoyl-L-tartaric acid for resolution, and the yield of the final product is low. Contents of the inve...

Claims

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Application Information

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IPC IPC(8): C07D211/60
CPCY02P20/55
Inventor 李雁武王敬
Owner CHONGQING MEDICAL UNIVERSITY
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