methyl 2-[[(4-fluorophenyl)sulfonyl]amino]-3,5-dimethylbenzoate -Drug Synthesis Database

【结构式】

【分子编号】47142

【品名】methyl 2-[[(4-fluorophenyl)sulfonyl]amino]-3,5-dimethylbenzoate

【CA登记号】

【分子式】C₁₆H₁₆FNO₄S

【分子量】337.3717832

【元素组成】C 56.96% H 4.78% F 5.63% N 4.15% O 18.97% S 9.5%

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 4-fluorobenzenesulfonyl chloride (I) with anthranilic acid derivative (II) by means of pyridine yields sulfonamide derivative (III), which is then N-alkylated by reaction with benzyl bromide (IV) by means of NaH in DMF to furnish compound (V). Saponification of the methyl ester group of (V) by treatment with NaOH in refluxing MeOH affords carboxylic acid (VI) (1), which is then converted into compound (X) by condensation with hydroxy derivative (IX) by means of NaH in DMF. (In turn, compound (IX) can be obtained by coupling of 2-benzofurancarboxylic acid (VII) with ethanolamine (VIII) by means of HOBt/EDC and NMM in DMF. Finally, the target product is obtained by derivatization of the carboxylic acid moiety of (X) with hydroxylamine hydrochloride by means of HOBt/EDC and Et3N in DMF.

参考文献中间体

合成目标

【2】 Gu, Y.; Nelson, F.C.; Zask, A.; Du, M.T.; Levin, J.I.; Venkatesan, M. (American Cyanamid Co.); Preparation and use of orthosulfonamido aryl hydroxamic acids as matrix metalloproteinase and TACE inhibitors. US 5929097 .
【1】 Levin, J.I.; Nilakantan, R.; Mobilio, D.; Chen, J.M.; Nelson, F.C.; Powers, R.; Moy, F.J.; Zask, A.; Structure-based design of a novel, potent, and selective inhibitor for MMP-13 utilizing NMR spectroscopy and computer-aided molecular design. J Am Chem Soc 2000, 122, 40, 9648.

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)	12292	4-Fluorobenzenesulfonyl chloride	349-88-2	C₆H₄ClFO₂S	详情	详情
(II)	47141	methyl 2-amino-3,5-dimethylbenzoate		C₁₀H₁₃NO₂	详情	详情
(III)	47142	methyl 2-[[(4-fluorophenyl)sulfonyl]amino]-3,5-dimethylbenzoate		C₁₆H₁₆FNO₄S	详情	详情
(IV)	12912	1-(Bromomethyl)benzene; Alpha-bromotoluene	100-39-0	C₇H₇Br	详情	详情
(V)	47143	methyl 2-[benzyl[(4-fluorophenyl)sulfonyl]amino]-3,5-dimethylbenzoate		C₂₃H₂₂FNO₄S	详情	详情
(VI)	47144	2-[benzyl[(4-fluorophenyl)sulfonyl]amino]-3,5-dimethylbenzoic acid		C₂₂H₂₀FNO₄S	详情	详情
(VII)	38339	Benzofuran-2-carboxylic acid; 1-benzofuran-2-carboxylic acid	496-41-3	C₉H₆O₃	详情	详情
(VIII)	10259	Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol；2-Aminoethyl alcohol	141-43-5	C₂H₇NO	详情	详情
(IX)	47145	N-(2-hydroxyethyl)-1-benzofuran-2-carboxamide		C₁₁H₁₁NO₃	详情	详情
(X)	47146	2-[[(4-[2-[(1-benzofuran-2-ylcarbonyl)amino]ethoxy]phenyl)sulfonyl](benzyl)amino]-3,5-dimethylbenzoic acid		C₃₃H₃₀N₂O₇S	详情	详情

Extended Information