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【结 构 式】

【分子编号】34576

【品名】methyl 2-[2-([[4-(2-chlorophenyl)-1,3-thiazol-2-yl]amino]carbonyl)-1H-indol-1-yl]acetate

【CA登记号】

【 分 子 式 】C21H16ClN3O3S

【 分 子 量 】425.89516

【元素组成】C 59.22% H 3.79% Cl 8.32% N 9.87% O 11.27% S 7.53%

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:(VII)

The esterification of indole-2-carboxylic acid (I) with benzyl alcohol and CDI gives the corresponding benzyl ester (II), which is alkylated with methyl bromoacetate (III) by means of NaH in DMF yielding 1-(methoxycarbonylmethyl)-1H-indole-2-carboxylic acid benzyl ester (IV). The debenzylation of (IV) with H2 over Pd/C in ethanol/DMF affords the free acid (V), which is condensed with 4-(2-chlorophenyl)thiazol-2-amine (VI) by means of benzotriazolyloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP) in DMF to give the carboxamide (VII). Finally, the ester group of (VII) is hydrolyzed with NaOH or KOH in methanol/water.

1 Bras, J.-P.; Frehel, D.; Gully, D.; Valette, G. (Sanofi-Synthélabo ); Heterocyclic derivs. of acylaminothiazole, their preparation and pharmaceutical compsns. containing them. EP 0432040; FR 2655344; FR 2661677; JP 1991279374; JP 1998130147; US 5189049 .
2 Radisson, J. (Sanofi-Synthelabo ); Method for preparing lintitript potassium salt. FR 2781227; WO 0005233 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
18710 Benzyl alcohol; Phenylmethanol 100-51-6 C7H8O 详情 详情
(I) 25226 1H-Indole-2-carboxylic acid; Indole-2-carboxylic acid 1477-50-5 C9H7NO2 详情 详情
(II) 34572 benzyl 1H-indole-2-carboxylate C16H13NO2 详情 详情
(III) 12309 methyl 2-bromoacetate; methyl bromoacetate 96-32-2 C3H5BrO2 详情 详情
(IV) 34573 benzyl 1-(2-methoxy-2-oxoethyl)-1H-indole-2-carboxylate C19H17NO4 详情 详情
(V) 34574 1-(2-methoxy-2-oxoethyl)-1H-indole-2-carboxylic acid C12H11NO4 详情 详情
(VI) 34575 4-(2-chlorophenyl)-1,3-thiazol-2-ylamine; 4-(2-chlorophenyl)-1,3-thiazol-2-amine C9H7ClN2S 详情 详情
(VII) 34576 methyl 2-[2-([[4-(2-chlorophenyl)-1,3-thiazol-2-yl]amino]carbonyl)-1H-indol-1-yl]acetate C21H16ClN3O3S 详情 详情
(VIII) 34577 2-bromo-1-(2-chlorophenyl)-1-ethanone C8H6BrClO 详情 详情
(IX) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
Extended Information