4-{[(4-methoxy-4-oxobutanoyl)amino]sulfonyl}benzenediazonium chloride -Drug Synthesis Database

【结构式】

【分子编号】55810

【品名】4-{[(4-methoxy-4-oxobutanoyl)amino]sulfonyl}benzenediazonium chloride

【CA登记号】

【分子式】C₁₁H₁₂ClN₃O₅S

【分子量】333.7522

【元素组成】C 39.59% H 3.62% Cl 10.62% N 12.59% O 23.97% S 9.61%

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：(V)

The condensation of 4-nitrobenzenesulfonamide (I) with 4-chloro-4-oxobutyric acid methyl ester (II) in refluxing pyridine gives 4-(4-nitrobenzenesulfonamido)-4-oxobutyric acid methyl ester (III), which is reduced with Fe and NH4Cl in methanol/water to yield the corresponding 4-amino derivative (IV). The diazotization of (IV) with NaNO2 and HCl affords the diazonium salt (V), which is condensed with 2-hydroxybenzoic acid (VI) to provide the azo compound (VII). Finally, this compound is hydrolyzed with NaOH to the target succinamic acid derivative.

参考文献中间体

合成目标

【1】 Riggs-Sauthier, J.A.; Malson, E.; Harris, M.; Myung, S.; Liddle, R.; Ekwuribe, N.; Synthesis and activity of novel 5-aminosalicylic acid (5-ASA)-containing prodrugs for the treatment of inflammatory bowel disease. 224th ACS Natl Meet (Aug 18 2002, Boston) 2002, Abst MEDI 305.
【2】 Ekwuribe, N.N.; Malson, E.; Riggs-Sauthier, J. (Nobex Corp.); 5-ASA derivs. having anti-inflammatory and antibiotic activity and methods of treating diseases therewith. US 6458776; WO 0218330 .

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)	55807	4-Nitrobenzenesulfonamide; p-Nitrobenzenesulfonamide	6325-93-5	C₆H₆N₂O₄S	详情	详情
(II)	18060	4-Chloro-4-oxobutyric acid methyl ester; 3-Carbomethosypropionyl chloride; Methyl 4-chloro-4-oxobutanoate	1490-25-1	C₅H₇ClO₃	详情	详情
(III)	55808	methyl 4-{[(4-nitrophenyl)sulfonyl]amino}-4-oxobutanoate		C₁₁H₁₂N₂O₇S	详情	详情
(IV)	55809	methyl 4-{[(4-aminophenyl)sulfonyl]amino}-4-oxobutanoate		C₁₁H₁₄N₂O₅S	详情	详情
(V)	55810	4-{[(4-methoxy-4-oxobutanoyl)amino]sulfonyl}benzenediazonium chloride		C₁₁H₁₂ClN₃O₅S	详情	详情
(VI)	15240	2-Hydroxybenzoic acid; Salicylic acid	69-72-7	C₇H₆O₃	详情	详情
(VII)	55811	2-hydroxy-5-[(E)-2-(4-{[(4-methoxy-4-oxobutanoyl)amino]sulfonyl}phenyl)diazenyl]benzoic acid		C₁₈H₁₇N₃O₈S	详情	详情

Extended Information