dimethyl 7-chloro-4-oxo-1,4-dihydro-2,3-quinolinedicarboxylate -Drug Synthesis Database

【结构式】

【分子编号】58494

【品名】dimethyl 7-chloro-4-oxo-1,4-dihydro-2,3-quinolinedicarboxylate

【CA登记号】

【分子式】C₁₃H₁₀ClNO₅

【分子量】295.67884

【元素组成】C 52.81% H 3.41% Cl 11.99% N 4.74% O 27.06%

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：(III)

Condensation of methyl 4-chloroanthranilate (I) with dimethyl butynedioate (II), followed by cyclization in the presence of potassium tert-butoxide leads to the quinolone dicarboxylate (III). Partial hydrolysis of diester (III) under basic conditions affords mono-acid (IV), which is converted to acid chloride (V) by treatment with SOCl2. Condensation of acid chloride (V) with pyrrolidine provides the corresponding amide (VI). The methyl ester group of (VI) is subsequently hydrolyzed with NaOH to afford the intermediate acid (VII).

参考文献中间体

合成目标

【1】 Horchler, C.L.; et al.; Synthesis of 7-chloro-4-hydroxy-2-(3-(aryl/heteroaryl)prop-2-ynyl)1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-diones (PQD I); potent oral glycine antagonists. 28th Natl Med Chem Symp (June 8 2002, San Diego) 2002, Abst 19.

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)	49161	4-Chloroanthranilic acid methyl ester; Methyl 4-chloroanthranilate; Methyl 2-amino-4-chlorobenzoate; 2-Amino-4-chlorobenzoic acid methyl ester	5900-58-3	C₈H₈ClNO₂	详情	详情
(II)	24551	Dimethyl acetylenedicarboxylate; Dimethyl 2-butynedioate;Acetylenedicarboxylic acid dimethyl ester	762-42-5	C₆H₆O₄	详情	详情
(III)	58494	dimethyl 7-chloro-4-oxo-1,4-dihydro-2,3-quinolinedicarboxylate		C₁₃H₁₀ClNO₅	详情	详情
(IV)	58495	7-chloro-3-(methoxycarbonyl)-4-oxo-1,4-dihydro-2-quinolinecarboxylic acid		C₁₂H₈ClNO₅	详情	详情
(V)	58496	methyl 7-chloro-2-(chlorocarbonyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylate		C₁₂H₇Cl₂NO₄	详情	详情
(VI)	58497	methyl 7-chloro-4-oxo-2-(1-pyrrolidinylcarbonyl)-1,4-dihydro-3-quinolinecarboxylate		C₁₆H₁₅ClN₂O₄	详情	详情
(VII)	58498	7-chloro-4-oxo-2-(1-pyrrolidinylcarbonyl)-1,4-dihydro-3-quinolinecarboxylic acid		C₁₅H₁₃ClN₂O₄	详情	详情

Extended Information