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【结 构 式】 
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【分子编号】24957 【品名】tert-butyl 2-[(2-[2-[(2-hydroxyethyl)amino]ethyl]-6-oxo-2,6-dihydroindazolo[4,3-gh]isoquinolin-5-yl)amino]ethyl(methyl)carbamate 【CA登记号】 |
【 分 子 式 】C25H32N6O4 【 分 子 量 】480.56712 【元素组成】C 62.48% H 6.71% N 17.49% O 13.32% |
合成路线1
该中间体在本合成路线中的序号：(VIII)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.
| 【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 |