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【结 构 式】

【分子编号】32926

【品名】4-cyclohexylbutyric acid

【CA登记号】4441-63-8

【 分 子 式 】C10H18O2

【 分 子 量 】170.25172

【元素组成】C 70.55% H 10.66% O 18.79%

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:(XVIII)

4-Cyclohexylbutyric acid (XVIII) was converted to the corresponding acid chloride (XIX) with SOCl2. Subsequent Friedel-Crafts condensation with 2,5-dimethoxychlorobenzene (XX) yielded ketone (XXI). After bromination of (XXI) in CH2Cl2, the resulting bromoketone (XXII) was condensed with thiourea (XXIII), providing aminothiazole (XXIV). This amine was coupled with indole acid (XV) by means of BOP to give amide (XXV). The title compound was then obtained by deprotection of the tert-butyl ester with trifluoroacetic acid. In a related alternative procedure, coupling of aminothiazole (XXIV) with indole acid (XVII) gave amide (XXVI). The methyl ester was then deprotected by hydrolysis with K2CO3 in aqueous butanol.

1 Brodin, R.; Boigegrain, R.; Molimard, J.-C.; Bignon, E.; Olliero, D. (Sanofi-Synthelabo ); Carboxamidothiazole derivs., preparation, pharmaceutical compsns. containing them. EP 1017693; FR 2768737; FR 2777887; WO 9915525 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XV) 32923 1-[2-(tert-butoxy)-2-oxoethyl]-5,7-dimethyl-1H-indole-2-carboxylic acid C17H21NO4 详情 详情
(XVII) 32925 1-(2-methoxy-2-oxoethyl)-5,7-dimethyl-1H-indole-2-carboxylic acid C14H15NO4 详情 详情
(XVIII) 32926 4-cyclohexylbutyric acid 4441-63-8 C10H18O2 详情 详情
(XIX) 32927 4-cyclohexylbutanoyl chloride C10H17ClO 详情 详情
(XX) 32928 2-chloro-1,4-dimethoxybenzene; 2-chloro-4-methoxyphenyl methyl ether 2100-42-7 C8H9ClO2 详情 详情
(XXI) 32929 1-(4-chloro-2,5-dimethoxyphenyl)-4-cyclohexyl-1-butanone C18H25ClO3 详情 详情
(XXII) 32930 2-bromo-1-(4-chloro-2,5-dimethoxyphenyl)-4-cyclohexyl-1-butanone C18H24BrClO3 详情 详情
(XXIII) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(XXIV) 32931 4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-amine; 4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-ylamine C19H25ClN2O2S 详情 详情
(XXV) 32932 tert-butyl 2-[2-([[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]amino]carbonyl)-5,7-dimethyl-1H-indol-1-yl]acetate C36H44ClN3O5S 详情 详情
(XXVI) 32933 methyl 2-[2-([[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]amino]carbonyl)-5,7-dimethyl-1H-indol-1-yl]acetate C33H38ClN3O5S 详情 详情
Extended Information