Process for synthesizing antithrombin inhibitor of non-asymmetric non-peptide kind
An antithrombin, non-peptide technology, applied in the field of synthesis of new antithrombin inhibitors, can solve the problems of high price, low total yield, low yield, etc. high yield effect
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[0038] Example 1
[0039] Synthesis of 3-(pyridine-2-imine)-propionic acid ethyl ester (10)
[0040]Under nitrogen protection, add ethyl acrylate (27.5g, 0.275mol) to compound 9 (A=H, X=N)-2-aminopyridine (22.5g, 0.25mol), and stir and reflux for 24h at a temperature higher than 100℃ , The precipitate was filtered off, the residue was concentrated and purified with a silica gel column to obtain a white solid 10 (38 g, 72%).
[0041] Synthesis of 1-(4-cyano-aniline)-acetic acid (12)
[0042] Add 150ml of water to compound 11 (6.0g, 0.05mol) and 1-chloroacetic acid (10g, 0.11mol) and heat to reflux until a large amount of yellow solid precipitates out. Filter at room temperature and rinse with water, anhydrous ethanol, and anhydrous ether. After washing, 12 (6.4 g, 73%) is obtained as a yellow solid.
[0043] Synthesis of 4-aminomethyl-3-nitro-benzoic acid (1)
[0044] 150ml of 25%-30% methylamine aqueous solution was added to compound 13 (25g, 0.124mol), and the system was reacted ...
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[0059] Example 2
[0060] Synthesis of 3-(4-fluorophenyl-1-imine)-propionic acid ethyl ester (10′)
[0061] Under nitrogen protection, add ethyl acrylate (27.5g, 0.275mol) to compound 9'(A=F, X=H)-4-fluoroaniline (23.5g, 0.25mol), add 10ml of absolute ethanol and 10ml of three Ethylamine was stirred and refluxed at a temperature higher than 100°C for 24 hours, the precipitate was filtered off, and the residue was concentrated and purified with a silica gel column to obtain a light red solid 10' (43g, 77%).
[0062] Synthesis of 3-[(4-aminomethyl-3-nitro-benzoyl)-(4-fluorobenzene)-2-imine]-propionic acid ethyl ester (3′)
[0063] Dissolve compound 10' (10.5g, 0.05mol) in 30ml CH 2 Cl 2 And 30ml triethylamine, slowly add the CH of compound 2 at room temperature 2 Cl 2 Solution. The mixed system was allowed to react at room temperature for 12 hours, the precipitate was filtered off, and the residue was concentrated and purified with a silica gel column to obtain a yellow oily liquid ...
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