10-chloro-6-methyl-5H-pyrido[3',4':4,5]pyrrolo[2,3-g]isoquinoline -Drug Synthesis Database

【结构式】

【分子编号】29976

【品名】10-chloro-6-methyl-5H-pyrido[3',4':4,5]pyrrolo[2,3-g]isoquinoline

【CA登记号】

【分子式】C₁₅H₁₀ClN₃

【分子量】267.71732

【元素组成】C 67.3% H 3.76% Cl 13.24% N 15.7%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(XIV)

Compound (X) is reduced with H2 over Pd/C in acetic acid to 1-hydroxy-5-methyl-6-[(3-amino-4-pyridyl)amino]isoquinolin (Xl). The treatment of (XI) with NaNO2 in acetic acid yields 1-(1-hydroxy-5-methyl-6-isoquinolyl)triazolo[4,5-c]pyridine (XII), which is converted into 1-hydroxy-5-methyldipyrido[4,3-b][3,4-f]indole (XIII). The reaction of (XIII) with PCl5 in refluxing POCl3 gives 1-chloro-5-methyldipyrido[4,3-b][3,4-f]indole (XIV), which is finally condensed with 3-(diethylamino)propylamine (XV) by heating at 150 C.

参考文献中间体

合成目标

【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】 Van der Burg, W.J. (Akzo Nobel N.V.); Tetracyclic compounds. BE 0840362; CH 622261; DE 2614406; DK 142498; ES 446634; FR 2305986; GB 1543171; JP 76122099; NL 754075 .
【3】 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
(XI)	29973	6-[(3-amino-4-pyridinyl)amino]-5-methyl-1-isoquinolinol		C₁₅H₁₄N₄O	详情	详情
(XII)	29974	5-methyl-6-(1H-[1,2,3]triazolo[4,5-c]pyridin-1-yl)-1-isoquinolinol		C₁₅H₁₁N₅O	详情	详情
(XIII)	29975	6-methyl-5H-pyrido[3',4':4,5]pyrrolo[2,3-g]isoquinolin-10-ol		C₁₅H₁₁N₃O	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

合成路线2

该中间体在本合成路线中的序号：(XIV)

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.

参考文献中间体

合成目标

【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

Extended Information