1-chloro-7-methoxy-4-nitro-9(10H)-acridinone -Drug Synthesis Database

【结构式】

【分子编号】53914

【品名】1-chloro-7-methoxy-4-nitro-9(10H)-acridinone

【CA登记号】

【分子式】C₁₄H₉ClN₂O₄

【分子量】304.68924

【元素组成】C 55.19% H 2.98% Cl 11.64% N 9.19% O 21%

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：(IV)

The condensation of 4-methoxyaniline (I) with 2,6-dichloro-3-nitrobenzoic acid (II) by means of DIEA or N,N-dimethylaniline at 75 C gives 6-chloro-2-(4-methoxyphenylamino)-3-nitrobenzoic acid (III), which is cyclized in refluxing POCl3 to yield the acridone (IV). Finally, this compound is condensed with N-[3-(dimethylamino)propyl]hydrazine (V) in THF/methanol to afford the target 2,6-dihydro-pyrazolo[3,4,5-kl]acridine.

参考文献中间体

合成目标

【1】 Capps, D.B. (Pfizer Inc.); Pyrazolo[3,4,5-kl]acridine cpds., pharmaceutical compsns. the same and processes for their production. EP 0138302; ES 8701758; ES 8703468; ES 8703874; ES 8703875; JP 1985069084; JP 1994041127; US 4555572 .
【2】 Capps, D.B.; et al.; 2-(Aminoalkyl)-5-nitropyrazolo[3,4,5-kl]acridines, a new class of anticancer agents. J Med Chem 1992, 35, 26, 4770.

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)	10478	p-Anisidine; 4-Methoxyaniline; 4-Methoxyphenylamine	104-94-9	C₇H₉NO	详情	详情
(II)	52274	2,5-Dichloro-3-nitrobenzoic acid	88-86-8	C₇H₃Cl₂NO₄	详情	详情
(III)	53913	6-Chloro-2-(4-methoxyphenylamino)-3-nitrobenzoic acid		C₁₄H₁₁ClN₂O₅	详情	详情
(IV)	53914	1-chloro-7-methoxy-4-nitro-9(10H)-acridinone		C₁₄H₉ClN₂O₄	详情	详情
(V)	53915	3-hydrazino-N,N-dimethyl-1-propanamine; N-(3-hydrazinopropyl)-N,N-dimethylamine		C₅H₁₅N₃	详情	详情

Extended Information