2-methylbenzenesulfonamide -Drug Synthesis Database

【结构式】

【分子编号】63841

【品名】2-methylbenzenesulfonamide

【CA登记号】

【分子式】C₇H₉NO₂S

【分子量】171.22

【元素组成】C 49.1% H 5.3% N 8.18% O 18.69% S 18.73%

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：(X)

A modification of Leimgruber-Batcho synthesis of indoles was employed to convert 3-methyl-4-nitrobenzoic acid (I) to the 3,5-disubstituted indole (V)). In this process, the intermediate enamine (II) was alkylated with the bromobenzoate (III) prior to hydrolysis and reductive cyclization to the indole nucleus. Alkylation of (V) with iodomethane under basic conditions, followed by amide formation using (R)-4,4,4-trifluoro-2-methylbutylamine (VII) afforded the key intermediate amidoester (VIII). Hydrolysis of the methyl ester moiety of (VIII) with aqueous lithium hydroxide, followed by sulfonimide formation gave ZD 3523).

参考文献中间体

合成目标

【1】 Bernstein, P.R.; Jacobs, R.T.; ZD 3523. Drugs Fut 1995, 20, 12, 1233.
【2】 Jacobs, R.T.; Costello, G.F.; Brook, S.A.; Harrison, P.J. (AstraZeneca plc); A process for the preparation of a 3-alkylated indole, intermediates, and a process for the preparation of a derivative thereof. EP 0489547 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	14771	(4-carboxy-2-methylphenyl)(oxo)-lambda(5)-azanolate	C₈H₈NO₄	详情	详情
(II)	14772	[4-carboxy-2-[(E)-2-(dimethylamino)ethenyl]phenyl](oxo)-lambda(5)-azanolate	C₁₁H₁₃N₂O₄	详情	详情
(III)	11920	methyl 4-(bromomethyl)-3-methoxybenzoate; 4-(Bromomethyl)-3-methoxy benzoic acid methyl ester	C₁₀H₁₁BrO₃	详情	详情
(IV)	14774	(4-carboxy-2-[1-formyl-2-[2-methoxy-4-(methoxycarbonyl)phenyl]ethyl]phenyl)(oxo)-lambda(5)-azanolate	C₁₉H₁₈NO₈	详情	详情
(V)	14775	3-[2-methoxy-4-(methoxycarbonyl)benzyl]-1H-indole-5-carboxylic acid	C₁₉H₁₇NO₅	详情	详情
(VI)	14776	3-[2-methoxy-4-(methoxycarbonyl)benzyl]-1-methyl-1H-indole-5-carboxylic acid	C₂₀H₁₉NO₅	详情	详情
(VII)	14777	(2R)-4,4,4-trifluoro-2-methyl-1-butanamine; (2R)-4,4,4-trifluoro-2-methylbutylamine	C₅H₁₀F₃N	详情	详情
(VIII)	14778	methyl 3-methoxy-4-[[1-methyl-5-([[(2R)-4,4,4-trifluoro-2-methylbutyl]amino]carbonyl)-1H-indol-3-yl]methyl]benzoate	C₂₅H₂₇F₃N₂O₄	详情	详情
(IX)	14779	3-methoxy-4-[[1-methyl-5-([[(2R)-4,4,4-trifluoro-2-methylbutyl]amino]carbonyl)-1H-indol-3-yl]methyl]benzoic acid	C₂₄H₂₅F₃N₂O₄	详情	详情
(X)	63841	2-methylbenzenesulfonamide	C₇H₉NO₂S	详情	详情

Extended Information