1-(7-chloro-4-quinolinyl)-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-carboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】41279

【品名】1-(7-chloro-4-quinolinyl)-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-carboxylic acid

【CA登记号】

【分子式】C₂₁H₁₆ClN₃O₄

【分子量】409.82856

【元素组成】C 61.55% H 3.94% Cl 8.65% N 10.25% O 15.62%

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：(VI)

The condensation of 2',6'-dimethoxyacetophenone (I) with diethyl oxalate (II) by means of sodium methoxide in refluxing methanol gives the dioxobutyrate (III), which is cyclized with 7-chloroquinoline-4-hydrazine (IV) in refluxing acetic acid yielding the pyrazole derivative (V). The hydrolysis of the ester group of (V) with KOH in refluxing methanol/water affords the corresponding carboxylic acid (VI), which is finally treated with SOCl2 in refluxing toluene and condensed with 2-aminoadamantane-2-carboxylic acid.

参考文献中间体

合成目标

【1】 Boigegrain, R.; Gully, D.; Jeanjean, F.; Molimard, J.-C. (Sanofi-Synthélabo ); Amido-3-pyrazole derivs., process for their preparation and pharmaceutical compsns. containing them. EP 0477049; FR 2665898; JP 1992244065; US 5420141; US 5607958; US 5616592; US 5635526; US 5744491; US 5744493 .
【2】 Maffrand, J.P.; Gully, D.; Boigegrain, R.; Soubrie, P.; Kitabgi, P.; Rostene, W.; Le Fur, G.; Neurotensin receptor agonists and antagonists. Drugs Fut 1993, 18, 12, 1137.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	41280	2-amino-2-adamantanecarboxylic acid		C₁₁H₁₇NO₂	详情	详情
(I)	41275	1-(2,6-dimethoxyphenyl)-1-ethanone	2040-04-2	C₁₀H₁₂O₃	详情	详情
(II)	17571	Diethyl oxalate; Ethyl 2-ethoxy-2-oxoacetate	95-92-1	C₆H₁₀O₄	详情	详情
(III)	41276	sodium (Z)-4-(2,6-dimethoxyphenyl)-1-methoxy-1,4-dioxo-2-buten-2-olate		C₁₃H₁₃NaO₆	详情	详情
(IV)	41277	7-chloro-4-hydrazinoquinoline	23834-14-2	C₉H₈ClN₃	详情	详情
(V)	41278	methyl 1-(7-chloro-4-quinolinyl)-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-carboxylate		C₂₂H₁₈ClN₃O₄	详情	详情
(VI)	41279	1-(7-chloro-4-quinolinyl)-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-carboxylic acid		C₂₁H₁₆ClN₃O₄	详情	详情

Extended Information