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【结 构 式】 
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【分子编号】36275 【品名】N-[2-(dimethylamino)ethyl]-9-methoxy-5,6,11-trimethyl-6H-pyrido[4,3-b]carbazole-1-carboxamide 【CA登记号】 |
【 分 子 式 】C24H28N4O2 【 分 子 量 】404.51208 【元素组成】C 71.26% H 6.98% N 13.85% O 7.91% |
合成路线1
该中间体在本合成路线中的序号：(V)The known pyridocarbazole (I) was methylated to (II) using dimethyl carbonate as the alkylating agent in the presence of K2CO3 and the phase-transfer catalyst adogen-464. For the preparation of the required amide (V), the ester group of (III) was first hydrolyzed with NaOH to the carboxylic acid (III), which was then coupled with 2-(dimethylamino)ethyl amine (IV) by means of (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP) in hot N-methylpyrrolidone yielding (V). Finally, cleavage of the methyl ether of (V) with BBr3 provided the title compound.
| 【1】 Charton, Y.; Guilbaud, N.; Léonce, S.; Pierré, A.; Guillonneau, C.; Michel, A.; Atassi, G.; Kraus-Berthier, L.; Bisagni, E.; Synthesis of 9-O-substituted derivatives of 9-hydroxy-5, 6-dimethyl-6H-pyrido[4,3-b]carbazole-1-carboxylic acid (2-(dimethylamino)ethyl)amide and their 10- and 11-methyl analogues with improved antitumor activity. J Med Chem 1999, 42, 12, 2191. |
| 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) | 36272 | ethyl 9-methoxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazole-1-carboxylate | C21H20N2O3 | 详情 | 详情 | |
| (II) | 36273 | ethyl 9-methoxy-5,6,11-trimethyl-6H-pyrido[4,3-b]carbazole-1-carboxylate | C22H22N2O3 | 详情 | 详情 | |
| (III) | 36274 | 9-methoxy-5,6,11-trimethyl-6H-pyrido[4,3-b]carbazole-1-carboxylic acid | C20H18N2O3 | 详情 | 详情 | |
| (IV) | 14881 | N-(2-aminoethyl)-N,N-dimethylamine; N(1),N(1)-dimethyl-1,2-ethanediamine; 2-Dimethylaminoethylamine | 108-00-9 | C4H12N2 | 详情 | 详情 |
| (V) | 36275 | N-[2-(dimethylamino)ethyl]-9-methoxy-5,6,11-trimethyl-6H-pyrido[4,3-b]carbazole-1-carboxamide | C24H28N4O2 | 详情 | 详情 |