Azasetron hydrochloride CAS 123040-69-7
Introduction：Basic information about Azasetron hydrochloride CAS 123040-69-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Azasetron hydrochloride Basic information
| Product Name: | Azasetron hydrochloride |
| Synonyms: | N-1-AZABICYCLO[2.2.2]-OCT-3-YL-6-CHLORO-3,4-DIHYDRO-4-METHYL-3-OXO-2H-1,4-BENZOXAZINE-8-CARBOXAMIDE, HYDROCHLORIDE;N-(1-AZABICYCLO[2.2.2]OCT-3-YL)-6-CHLORO-4-METHYL-3-OXO-3,4-DIHYDRO-2H-1,4-BENZOXAZINE-8-CARBOXAMIDE HCL;N-(1-AZABICYCLO[2.2.2]OCT-3-YL)-6-CHLORO-4-METHYL-3-OXO-3,4-DIHYDRO-2H-1,4-BENZOXAZINE-8-CARBOXAMIDE HYDROCHLORIDE;Y-25130;Y-25130 HYDROCHLORIDE;AZASETRON HCL;Azasetron base;6-chloro-3-keto-4-methyl-N-quinuclidin-3-yl-1,4-benzoxazine-8-carboxamide |
| CAS: | 123040-69-7 |
| MF: | C17H20ClN3O3 |
| MW: | 349.81 |
| EINECS: | 1533716-785-6 |
| Product Categories: | Intermediates & Fine Chemicals;Pharmaceuticals;anti-emetic;Active Pharmaceutical Ingredients |
| Mol File: | 123040-69-7.mol |
Azasetron hydrochloride Chemical Properties
| Melting point | 301-303°C |
| Boiling point | 558.0±50.0 °C(Predicted) |
| density | 1.42±0.1 g/cm3(Predicted) |
| storage temp. | -20°C Freezer |
| pka | 13.31±0.20(Predicted) |
| CAS DataBase Reference | 123040-69-7(CAS DataBase Reference) |
Safety Information
| Chemical Properties | White to Off-White Solid |
| Originator | Azasetron,Pharm Chemical |
| Uses | As a 5-HT3 receptor antagonist, Azasetron hydrochloride can be used as an antiemetic. |
| Definition | ChEBI: Azasetron hydrochloride is a benzoxazine. |
| Manufacturing Process | To a solution of 2-(2-carboxy-4-chlorophenoxy)acetic acid in concentratedsulfuric acid is added dropwise a mixed liquid of fuming nitric acid andconcentrated sulfuric acid under stirring with keeping at a temperature below10°C. After the addition, the reaction mixture is stirred and poured into 10 Lof ice-cold water. The precipitated crystals are collected by filtration, washedwith 2 L of water four times and them dried to give 2-(2-carboxy-4-chloro-6-nitrophenoxy)acetic acid. To a solution of ferrous sulfate heptahydrate in of hot water is added asolution of 2-(2-carboxy-4-chloro-6-nitrophenoxy)acetic acid and aqueousconcentrated ammonia solution in water under stirring. After stirring, to thereaction mixture is twice added aqueous concentrated ammonia solution.While the reaction mixture becomes exothermic, stirring is continued. Theresultant mixture is filtered through a celite layer under reduced pressure andwashed with hot water twice. The filtrate is cooled and made acid withconcentrated hydrochloric acid. The precipitated crystals are washed withwater and dried to give 6-chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid. A mixture of 6-chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxylicacid, methanol and concentrated sulfuric acid is refluxed under heating withstirring, and then cooled. The precipitated crystals are collected by filtration,washed with methanol and dried to give methyl 6-chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxylate, melting point 239°-241°C. To a solution of methyl 6-chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxylate in dimethylformamide is added potassium t-butoxide and solutionstirred at room temperature. To the resultant solution is added dropwise asolution of methyl iodide in dimethylformainide under stirring. After thereaction solution is stirred, water is added thereto. The insoluble substance iscollected by filtration, washed with water and dried to give methyl 6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylate.A mixture of methyl 6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylate, ethanol and 4% aqueous potassium hydroxidesolution is refluxed with heating. The resultant solution is cooled and water isadded thereto followed by filtration. The filtrate is made acid withconcentrated hydrochloric acid. The precipitated crystals are collected byfiltration, washed with water and dried, and then recrystallized from ethanolto give 6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylicacid, melting point 241°-243°C. A solution of 6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid in tetrahydrofuran and dimethylformamide is cooled to below0°C and triethylamine is added under stirring thereto. Further, ethylchlorocarbonate is added and the mixture is stirred at room temperature. Tothe resultant mixture is added 3-amino-8-azabicyclo[3.2.1]octane and themixture stirred. After completion of the reaction, aqueous sodium hydrogencarbonate and ethyl acetate are added. The organic layer is separated,washed with water and dried over magnesium sulfate. The solvent is distilledoff to give 6-chloro-3,4-dihydro-4-methyl-N-(8-azabicyclo[3.2.1]oct-3-yl)-3-oxo-2H-1,4-benzoxazine-8-carboxamide.In practice it is usually used as hydrochloride. |
| Therapeutic Function | Antiemetic |
Azasetron hydrochloride Preparation Products And Raw materials
| Raw materials | Thionyl chloride-->Chloroform-->Sodium bicarbonate-->Ammonium chloride-->Iodomethane-->Chloroacetyl chloride-->4-Methylmorpholine-->3-METHOXYPROPIONIC ACID-->Methyl 5-chloro-2-hydroxybenzoate-->3-Aminoquinuclidine-->8-Azabicyclo[3.2.1]octan-3-amine(9CI)-->Ammonium nitrate-->Ethyl chloroformate-->Sulfuric acid-->Hydrochloric acid-->Nitric acid-->Ammonia-->Potassium tert-butoxide-->Potassium hydroxide-->Triethylamine |
