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【结 构 式】 
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【分子编号】29978 【品名】N-(1-chloro-5-methyl-6-isoquinolinyl)-N-(3-nitro-4-pyridinyl)amine; 1-chloro-5-methyl-N-(3-nitro-4-pyridinyl)-6-isoquinolinamine 【CA登记号】 |
【 分 子 式 】C15H11ClN4O2 【 分 子 量 】314.7308 【元素组成】C 57.24% H 3.52% Cl 11.26% N 17.8% O 10.17% |
合成路线1
该中间体在本合成路线中的序号：(XVI)1-hydroxy-5-methyl-6-[(3-nitro-4-pyridyl)amino]isoquinoline (X) is heated with phosphorous chloride oxide to give 1-chloro-5-methyl-6-[(3-nitro-4-pyridyl)amino]isoquinoline (XVI), which is reduced with H2 over Raney-Ni giving 6-[(3-amino-4-pyridyl)amino]-1-chloro-5-methylisoquinoline (XVII). This compound is treated with sodium nitrite to give 1-(1-chloro-5-methyl-6-isoquinolyl)triazolo[4,5-c]pyridine (XVIII), which is cyclized to 1-chloro-5-methylpyrido[4,3-b][3,4-f]indole (XIV), which is finally condensed with 3-(diethylamino)propylamine (XV) by heating at 150 C.
| 【1】 Rivalle, C.; Lhoste, J.M.; Bisagni, E.; Duerocq, C.; Synthesis of 10-substituted 5H-pyrido[3',4':4,5]pyrrolo[2,3-g]isoquinolines. J Chem Soc - Perkins Trans I 1979, 142-145. |
| 【2】 Hopkins, S.J.; Serradell, M.N.; Castaner, J.; BD-40. Drugs Fut 1984, 9, 2, 96. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (X) | 29972 | 5-methyl-6-[(3-nitro-4-pyridinyl)amino]-1-isoquinolinol | C15H12N4O3 | 详情 | 详情 | |
| (XIV) | 29976 | 10-chloro-6-methyl-5H-pyrido[3',4':4,5]pyrrolo[2,3-g]isoquinoline | C15H10ClN3 | 详情 | 详情 | |
| (XV) | 29977 | N-(3-aminopropyl)-N,N-diethylamine; N(1),N(1)-diethyl-1,3-propanediamine | 104-78-9 | C7H18N2 | 详情 | 详情 |
| (XVI) | 29978 | N-(1-chloro-5-methyl-6-isoquinolinyl)-N-(3-nitro-4-pyridinyl)amine; 1-chloro-5-methyl-N-(3-nitro-4-pyridinyl)-6-isoquinolinamine | C15H11ClN4O2 | 详情 | 详情 | |
| (XVII) | 29979 | N-(3-amino-4-pyridinyl)-N-(1-chloro-5-methyl-6-isoquinolinyl)amine; N(4)-(1-chloro-5-methyl-6-isoquinolinyl)-3,4-pyridinediamine | C15H13ClN4 | 详情 | 详情 | |
| (XVIII) | 29980 | 1-chloro-5-methyl-6-(1H-[1,2,3]triazolo[4,5-c]pyridin-1-yl)isoquinoline | C15H10ClN5 | 详情 | 详情 |