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【结 构 式】

【分子编号】14771

【品名】(4-carboxy-2-methylphenyl)(oxo)-lambda(5)-azanolate

【CA登记号】

【 分 子 式 】C8H8NO4

【 分 子 量 】182.15586

【元素组成】C 52.75% H 4.43% N 7.69% O 35.13%

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:(I)

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).

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 CAS号 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