6-chloro-9-fluorobenzo[g]isoquinoline-5,10-dione -Drug Synthesis Database

【结构式】

【分子编号】24950

【品名】6-chloro-9-fluorobenzo[g]isoquinoline-5,10-dione

【CA登记号】

【分子式】C₁₃H₅ClFNO₂

【分子量】261.6393432

【元素组成】C 59.68% H 1.93% Cl 13.55% F 7.26% N 5.35% O 12.23%

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：(I)

The synthesis of BBR-3438 has been described: The cyclization of 6-chloro-9-fluorobenz[g]isoquinoline-5,10-quinone (I) with 2-hydroxyethylhydrazine (II) in hot pyridine gives 2-(2-hydroxyethyl)-5-chloroindazolo[4,3-gh]isoquinolin-6(2H)-one (III), which is condensed with N-(2-aminoethyl)-N-methylcarbamic acid tert-butyl ester (IV) in hot pyridine yielding the corresponding 5-[2-[N-(tert-butoxycarbonyl)-N-methylamino]ethylamino] derivative (V). The mesylation of the OH group of (V) with mesyl chloride and triethylamine in dichloromethane affords the mesylate (VI), which is condensed with hot ethanolamine (VII) to give the protected compound (VIII). Finally, this compound is deprotected with HCl yielding BBR-3438.

参考文献中间体

合成目标

【1】 Krapcho, A.P.; Menta, E.; Oliva, A.; Di Domenico, R.; Fiocchi, L.; Maresch, M.E.; Gallagher, C.E.; Hacker, M.P.; Beggiolin, G.; Giuliani, F.C.; Pezzoni, G.; Spinelli, S.; Synthesis and antitumor evaluation of 2,5-disubstituted-indazolo[4,3-gh]isoquinolin-6(2H)-ones (9-aza-anthrapyrazoles). J Med Chem 1998, 41, 27, 5429.

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)	24950	6-chloro-9-fluorobenzo[g]isoquinoline-5,10-dione		C₁₃H₅ClFNO₂	详情	详情
(II)	24951	2-hydrazino-1-ethanol	109-84-2	C₂H₈N₂O	详情	详情
(III)	24952	5-chloro-2-(2-hydroxyethyl)indazolo[4,3-gh]isoquinolin-6(2H)-one		C₁₅H₁₀ClN₃O₂	详情	详情
(IV)	24953	N-(2-Aminoethyl)-N-methylcarbamic acid tert-butyl ester; tert-butyl 2-aminoethyl(methyl)carbamate	121492-06-6	C₈H₁₈N₂O₂	详情	详情
(V)	24954	tert-butyl 2-[[2-(2-hydroxyethyl)-6-oxo-2,6-dihydroindazolo[4,3-gh]isoquinolin-5-yl]amino]ethyl(methyl)carbamate		C₂₃H₂₇N₅O₄	详情	详情
(VI)	24955	2-[5-([2-[(tert-butoxycarbonyl)(methyl)amino]ethyl]amino)-6-oxoindazolo[4,3-gh]isoquinolin-2(6H)-yl]ethyl methanesulfonate		C₂₄H₂₉N₅O₆S	详情	详情
(VII)	10259	Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol；2-Aminoethyl alcohol	141-43-5	C₂H₇NO	详情	详情
(VIII)	24957	tert-butyl 2-[(2-[2-[(2-hydroxyethyl)amino]ethyl]-6-oxo-2,6-dihydroindazolo[4,3-gh]isoquinolin-5-yl)amino]ethyl(methyl)carbamate		C₂₅H₃₂N₆O₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

The synthesis of BBR-3409 has been described: The cyclization of 6-chloro-9-fluorobenz[g]isoquinoline-5,10-quinone (I) with 2-hydroxyethylhydrazine (II) in hot pyridine gives 2-(2-hydroxyethyl)-5-chloroindazolo[4,3-gh]isoquinolin-6(2H)-one (III), which is condensed with N-(2-aminoethyl)-N,N-dimethylamine (IV) in hot pyridine yielding the corresponding compound (V). The mesylation of the OH group of (V) with mesyl chloride and triethylamine in dichloromethane affords the mesylate (VI), which is condensed with hot ethanolamine (VII) to give BBR-3409.

参考文献中间体

合成目标

【1】 Krapcho, A.P.; Menta, E.; Oliva, A.; Di Domenico, R.; Fiocchi, L.; Maresch, M.E.; Gallagher, C.E.; Hacker, M.P.; Beggiolin, G.; Giuliani, F.C.; Pezzoni, G.; Spinelli, S.; Synthesis and antitumor evaluation of 2,5-disubstituted-indazolo[4,3-gh]isoquinolin-6(2H)-ones (9-aza-anthrapyrazoles). J Med Chem 1998, 41, 27, 5429.

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)	24950	6-chloro-9-fluorobenzo[g]isoquinoline-5,10-dione		C₁₃H₅ClFNO₂	详情	详情
(II)	24951	2-hydrazino-1-ethanol	109-84-2	C₂H₈N₂O	详情	详情
(III)	24952	5-chloro-2-(2-hydroxyethyl)indazolo[4,3-gh]isoquinolin-6(2H)-one		C₁₅H₁₀ClN₃O₂	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)	26315	5-[[2-(dimethylamino)ethyl]amino]-2-(2-hydroxyethyl)indazolo[4,3-gh]isoquinolin-6(2H)-one		C₁₉H₂₁N₅O₂	详情	详情
(VI)	26316	2-[5-[[2-(dimethylamino)ethyl]amino]-6-oxoindazolo[4,3-gh]isoquinolin-2(6H)-yl]ethyl methanesulfonate		C₂₀H₂₃N₅O₄S	详情	详情
(VII)	10259	Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol；2-Aminoethyl alcohol	141-43-5	C₂H₇NO	详情	详情

Extended Information