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【结 构 式】

【分子编号】60017

【品名】5-bromo-2-(bromomethyl)-7-methoxy-6H-pyrazolo[4,5,1-de]acridin-6-one

【CA登记号】

【 分 子 式 】C16H10Br2N2O2

【 分 子 量 】422.07568

【元素组成】C 45.53% H 2.39% Br 37.86% N 6.64% O 7.58%

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:(XXII)

An improved synthesis of the title compound has been developed. Methyl ester (XX) was prepared from the known indazolylbenzoate sodium salt (XIX) by alkylation with iodomethane and K2CO3. Benzylic bromination of (XX) using NBS in the presence of AIBN as the radical initiator furnished the bromomethyl derivative (XXI). The brominated ester (XXI) was cyclized with trifluoromethanesulfonic acid at 100 C to provide the pyrazoloacridone (XXII) along with some phenol analogue (XXIII). Complete cleavage of the methyl ether of (XXII) was then accomplished with HBr in AcOH at 70 C. Further bromination of (XXIII) with elemental bromine in dichloroethane gave the ortho-bromophenol (XXIV). Introduction of the hydroxy group at C-10 was carried out by a two step sequence involving oxidation of (XXIV) to quinone (XXV) with (diacetoxy)iodobenzene, followed by its reduction to the corresponding hydroquinone (XXVI) with tetrabutylammonium triacetoxyborohydride. Condensation of (XXVI) with N-benzylethanolamine (XXVII) yielded the tertiary amine (XXVIII). Further bromine displacement in (XXVIII) with 1,3-propanediamine (XVI) provided (XXIX). The remaining bromine and the N-benzyl protecting groups of (XXIX) were finally subjected to hydrogenolysis in the presence of Pd/C

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.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XVI) 19331 3-aminopropylamine; 1,3-propanediamine 109-76-2 C3H10N2 详情 详情
(XIX) 60014 2-(6-bromo-3-methyl-1H-indazol-1-yl)-6-methoxybenzoate C16H12BrN2O3 详情 详情
(XX) 60015 methyl 2-(6-bromo-3-methyl-1H-indazol-1-yl)-6-methoxybenzoate C17H15BrN2O3 详情 详情
(XXI) 60016 methyl 2-[6-bromo-3-(bromomethyl)-1H-indazol-1-yl]-6-methoxybenzoate C17H14Br2N2O3 详情 详情
(XXII) 60017 5-bromo-2-(bromomethyl)-7-methoxy-6H-pyrazolo[4,5,1-de]acridin-6-one C16H10Br2N2O2 详情 详情
(XXIII) 60018 5-bromo-2-(bromomethyl)-7-hydroxy-6H-pyrazolo[4,5,1-de]acridin-6-one C15H8Br2N2O2 详情 详情
(XXIV) 60019 5,8-dibromo-2-(bromomethyl)-7-hydroxy-6H-pyrazolo[4,5,1-de]acridin-6-one C15H7Br3N2O2 详情 详情
(XXV) 60005 5,8-dibromo-7-hydroxy-2-methyl-6H-pyrazolo[4,5,1-de]acridin-6-one C15H8Br2N2O2 详情 详情
(XXVI) 60007 5,8-dibromo-7,10-dihydroxy-2-methyl-6H-pyrazolo[4,5,1-de]acridin-6-one C15H8Br2N2O3 详情 详情
(XXVII) 25630 2-(benzylamino)-1-ethanol 104-63-2 C9H13NO 详情 详情
(XXVIII) 60020 2-{[benzyl(butyl)amino]methyl}-5,8-dibromo-7,10-dihydroxy-6H-pyrazolo[4,5,1-de]acridin-6-one C26H23Br2N3O3 详情 详情
(XXIX) 60021 5-[(3-aminopropyl)amino]-2-{[benzyl(butyl)amino]methyl}-8-bromo-7,10-dihydroxy-6H-pyrazolo[4,5,1-de]acridin-6-one C29H32BrN5O3 详情 详情
Extended Information