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【结 构 式】

【分子编号】24954

【品名】tert-butyl 2-[[2-(2-hydroxyethyl)-6-oxo-2,6-dihydroindazolo[4,3-gh]isoquinolin-5-yl]amino]ethyl(methyl)carbamate

【CA登记号】

【 分 子 式 】C23H27N5O4

【 分 子 量 】437.49868

【元素组成】C 63.14% H 6.22% N 16.01% O 14.63%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(V)

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
Extended Information