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【结 构 式】 
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【分子编号】24825 【品名】(1S,9R,17S)-6-chloro-12-methyl-16-oxo-2-oxa-12,15-diazatetracyclo[7.5.3.0(1,10).0(3,8)]heptadeca-3,5,7-triene-17-carboxylic acid 【CA登记号】 |
【 分 子 式 】C16H17ClN2O4 【 分 子 量 】336.77476 【元素组成】C 57.06% H 5.09% Cl 10.53% N 8.32% O 19% |
合成路线1
该中间体在本合成路线中的序号：(IV)This compound can be obtained by two related ways: 1) By cyclization of ethyl 6-chlorocoumarin-3-carboxylate (I) and N-methyl-4-piperiodone (II) by means of sodium acetate in refluxing ethanol, followed by a treatment with refluxing concentrated hydrochloric acid. 2) The cyclization of (I) and (II) by means of ammonium acetate in refluxing ethanol, followed by a treatment with cool concentrated hydrochloric acid gives the lactam od the ethyl monoester of 4a-amino-8-chloro-2-methyl-1,2,3,4,4a,10a-hexahydro(10H)-benzopyrano[3,2-c]pyrid-10-ylmalonic acid (III), which is hydrolyzed with KOH in refluxing ethanol-water to give the corresponding free acid (IV). Finally, this compound is decarboxylated by a treatment with NaHCO3 in refluxing water.
| 【1】 Baxter, M.G.; Elphick, A.R.; Miller, A.A.; Sawyer, D.A. (Glaxo Wellcome plc); 1,2,4-Triazine derivs., process for preparing such cpds., pharmaceutical compsns. and intermediates utilized for this process. CA 1133938; EP 0021121 . |
| 【2】 Castaner, J.; Prous, J.; Lortalamine. Drugs Fut 1986, 11, 5, 375. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 24822 | ethyl 6-chloro-2-oxo-2H-chromene-3-carboxylate | C12H9ClO4 | 详情 | 详情 | |
| (II) | 10919 | 1-Methyl-4-piperidone; 1-Methyltetrahydro-4(1H)-pyridinone; N-Methyl-4-piperidone;1-methylpiperidin-4-one | 1445-73-4 | C6H11NO | 详情 | 详情 |
| (III) | 24824 | ethyl (1S,9R,17S)-6-chloro-12-methyl-16-oxo-2-oxa-12,15-diazatetracyclo[7.5.3.0(1,10).0(3,8)]heptadeca-3,5,7-triene-17-carboxylate | C18H21ClN2O4 | 详情 | 详情 | |
| (IV) | 24825 | (1S,9R,17S)-6-chloro-12-methyl-16-oxo-2-oxa-12,15-diazatetracyclo[7.5.3.0(1,10).0(3,8)]heptadeca-3,5,7-triene-17-carboxylic acid | C16H17ClN2O4 | 详情 | 详情 |