Novel preparation method of azasetron hydrochloride
The invention provides a novel preparation method of azasetron hydrochloride, belonging to the technical field of medicine synthesis. According to the method, methyl 5-chlorosalicylate is used as a raw material; after acetic anhydride nitrification and stannous chloride reduction at room temperature...
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| creator | TANG KEHUI DONG HONGBO MENG JIAN DU WEIHONG CAO NING CAO SHENGHUA WANG YUCHI LUO HONGBING |
| description | The invention provides a novel preparation method of azasetron hydrochloride, belonging to the technical field of medicine synthesis. According to the method, methyl 5-chlorosalicylate is used as a raw material; after acetic anhydride nitrification and stannous chloride reduction at room temperature, dimethyl carbonate is used as a methylation reagent, and an intermediate V (6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylic acid methyl ester) is synthesized by adopting a one-pot method; the intermediate V is hydrolyzed to obtain 6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-formic acid (VI); and the compound reacts with free 3-aminoquinuclidine dihydrochloride for 1 h under the catalysis of TBTU to form a salt so as to obtain I (azasetron hydrochloride). According to the method, the yield of each step is high; aftertreatment is simple; the reaction time of each step is short; conditions are mild; low-toxicity environment-friendly reagents are adopted; energy consumption is reduced |
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According to the method, methyl 5-chlorosalicylate is used as a raw material; after acetic anhydride nitrification and stannous chloride reduction at room temperature, dimethyl carbonate is used as a methylation reagent, and an intermediate V (6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylic acid methyl ester) is synthesized by adopting a one-pot method; the intermediate V is hydrolyzed to obtain 6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-formic acid (VI); and the compound reacts with free 3-aminoquinuclidine dihydrochloride for 1 h under the catalysis of TBTU to form a salt so as to obtain I (azasetron hydrochloride). 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According to the method, methyl 5-chlorosalicylate is used as a raw material; after acetic anhydride nitrification and stannous chloride reduction at room temperature, dimethyl carbonate is used as a methylation reagent, and an intermediate V (6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylic acid methyl ester) is synthesized by adopting a one-pot method; the intermediate V is hydrolyzed to obtain 6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-formic acid (VI); and the compound reacts with free 3-aminoquinuclidine dihydrochloride for 1 h under the catalysis of TBTU to form a salt so as to obtain I (azasetron hydrochloride). According to the method, the yield of each step is high; aftertreatment is simple; the reaction time of each step is short; conditions are mild; low-toxicity environment-friendly reagents are adopted; energy consumption is reduced</abstract><oa>free_for_read</oa></addata></record> |
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| title | Novel preparation method of azasetron hydrochloride |
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