3-methoxy-5H-indeno[2,1-c]quinoline-6,7-dione -Drug Synthesis Database

【结构式】

【分子编号】17169

【品名】3-methoxy-5H-indeno[2,1-c]quinoline-6,7-dione

【CA登记号】

【分子式】C₁₇H₁₁NO₃

【分子量】277.27928

【元素组成】C 73.64% H 4% N 5.05% O 17.31%

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 1,3-dioxoindane-2-carboxylic acid ethyl ester (I) with m-anisidine (II) in refluxing toluene gives the corresponding amide (III), which is cyclized with polyphosphoric acid (PPA) at 120 C yielding 3-methoxy-6,7-dihydro-5H-indeno[2,1-c]quinoline-6,7-dione (IV). The reaction of (IV) with refluxing POCl3 affords the chloroketone (V), which is condensed with 2-(dimethylamino)ethylamine (VI) in pyridine at 100 C giving the aminoketone (VII). Finally, this compound is demethylated with concentrated HBr in refluxing acetic acid.

参考文献中间体

合成目标

【1】 Castañer, J.; Hoshi, A.; TAS-103. Drugs Fut 1998, 23, 5, 513.
【2】 Ishida, K.; Wakida, M.; Utsugi, T.; Okazaki, S.; Yamada, Y.; Asano, T.; Synthesis of novel indeno[2,1-c]quinolin-7-one derivatives and their topoisomerase inhibitory and antitumor activities. 17th Symp Med Chem/6th Annu Meet Div Med Chem/2nd Conf Drug Discov (Nov 19-21, Tsukuba) 1997, Abst 2-P-05..
【3】 Okazaki, S.; Asao, T.; Wakida, M.; Ishida, K.; Washinosu, M.; Utsugi, T.; Yamada, Y. (Taiho Pharmaceutical Co., Ltd.); Novel fused indan deriv. and pharmaceutically acceptable salt. EP 0713870; US 5710162; US 5733918; WO 9532187 .

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)	17166	ethyl 1,3-dioxo-2-indanecarboxylate		C₁₂H₁₀O₄	详情	详情
(II)	13704	3-Methoxyphenylamine; 3-Methoxyaniline; m-Anisidine	536-90-3	C₇H₉NO	详情	详情
(III)	17168	N-(3-methoxyphenyl)-1,3-dioxo-2-indanecarboxamide		C₁₇H₁₃NO₄	详情	详情
(IV)	17169	3-methoxy-5H-indeno[2,1-c]quinoline-6,7-dione		C₁₇H₁₁NO₃	详情	详情
(V)	17170	6-chloro-3-methoxy-7H-indeno[2,1-c]quinolin-7-one		C₁₇H₁₀ClNO₂	详情	详情
(VI)	14881	N-(2-aminoethyl)-N,N-dimethylamine; N(1),N(1)-dimethyl-1,2-ethanediamine; 2-Dimethylaminoethylamine	108-00-9	C₄H₁₂N₂	详情	详情
(VII)	17172	6-[[2-(dimethylamino)ethyl]amino]-3-methoxy-7H-indeno[2,1-c]quinolin-7-one		C₂₁H₂₁N₃O₂	详情	详情

Extended Information