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【结 构 式】

【分子编号】60012

【品名】5-[(3-aminopropyl)amino]-8-bromo-10-hydroxy-2-{[(2-hydroxyethyl)amino]methyl}-7-methoxy-6H-pyrazolo[4,5,1-de]acridin-6-one

【CA登记号】

【 分 子 式 】C21H24BrN5O4

【 分 子 量 】490.35686

【元素组成】C 51.44% H 4.93% Br 16.3% N 14.28% O 13.05%

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:(XVII)

Displacement of the benzylic bromide (XIII) with concomitant hydrolysis of the phenolic acetate with ethanolamine (XIV) gave amine (XV). A further aromatic bromide of (XV) was displaced with hot 1,3-propanediamine (XVI), yielding adduct (XVII). Hydrogenolysis of the remaining bromide of (XVII) using Pd/C furnished (XVIII). Finally, methyl ether cleavage in (XVIII) with hot HCl provided the title compound

1 Mimura, T.; Kato, N.; Sugaya, T.; Ikuta, M.; Kato, S.; Kuge, Y.; Tomioka, S.; Kasai, M.; An efficient synthesis of a new class of DNA intercalating antitumor 7,10-dihydroxy-6H-pyrazolo[4,5,1-de]acridin-6-ones. Synthesis (Stuttgart) 1999, 6, 947.
2 Mimura, Y.; Shida, Y.; Kasai, M.; Ashizawa, T.; Gomi, K. (Kyowa Hakko Kogyo Co., Ltd.); Pyrazoloacridone derivs.. EP 0487097; JP 1993001064; US 5220026 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XIII) 60010 5,8-dibromo-2-(bromomethyl)-7-methoxy-6-oxo-6H-pyrazolo[4,5,1-de]acridin-10-yl acetate C18H11Br3N2O4 详情 详情
(XIV) 10259 Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol;2-Aminoethyl alcohol 141-43-5 C2H7NO 详情 详情
(XV) 60011 5,8-dibromo-10-hydroxy-2-{[(2-hydroxyethyl)amino]methyl}-7-methoxy-6H-pyrazolo[4,5,1-de]acridin-6-one C18H15Br2N3O4 详情 详情
(XVI) 19331 3-aminopropylamine; 1,3-propanediamine 109-76-2 C3H10N2 详情 详情
(XVII) 60012 5-[(3-aminopropyl)amino]-8-bromo-10-hydroxy-2-{[(2-hydroxyethyl)amino]methyl}-7-methoxy-6H-pyrazolo[4,5,1-de]acridin-6-one C21H24BrN5O4 详情 详情
(XVIII) 60013 5-[(3-aminopropyl)amino]-10-hydroxy-2-{[(2-hydroxyethyl)amino]methyl}-7-methoxy-6H-pyrazolo[4,5,1-de]acridin-6-one C21H25N5O4 详情 详情
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