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【结 构 式】

【分子编号】29781

【品名】1-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]-2-bromo-1-ethanone

【CA登记号】

【 分 子 式 】C9H6BrClF3NO

【 分 子 量 】316.5046896

【元素组成】C 34.15% H 1.91% Br 25.25% Cl 11.2% F 18.01% N 4.43% O 5.06%

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:(V)

Chlorination of 4-amino-3-trifluoromethylbenzoic acid (I) gives 4-amino-3-chloro-5-trifluoromethylbenzoic acid (II), which is transformed in two steps to 4'-amino-3'-chloro-5'-trifluoromethylacetophenone (IV) by means of its acid chloride (III) and diethyl malonate. UV-catalyzed bromination with bromine in glacial acetic acid at 60-65 C gives the corresponding alpha-bromoketone (V). Reaction of (V) with tert-butylamine in isopropanol at 20 C leads to 4'-amino-2-tert-butylamino-3'-chloro-5'-trifluoromethylacetophenone (VI), which, without isolation, is reduced with sodium borohydride to the base (VII) of the title compound. The latter is obtained by treatment of (VII) with hydrochloric acid in diethyl ether. The optical isomers of mabuterol have been separated via the diastereomeric esters obtained by treating the racemate with (-)-methoxvcarbonyl chloride.

1 Kruger, G.; Keck, J.; Noll, K.; Pieper, H.; Synthesis of futher amino-halogen substituted phenylaminoethanols. Arzneim-Forsch Drug Res 1984, 34, 11a, 1612.
2 Kruger, G.; Engelhardt, G.; Mabuterol Hydrochloride. Drugs Fut 1985, 10, 11, 913.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 16829 Diethyl malonate 105-53-3 C7H12O4 详情 详情
(I) 29777 4-amino-3-(trifluoromethyl)benzoic acid C8H6F3NO2 详情 详情
(II) 29778 4-amino-3-chloro-5-(trifluoromethyl)benzoic acid C8H5ClF3NO2 详情 详情
(III) 29779 4-amino-3-chloro-5-(trifluoromethyl)benzoyl chloride C8H4Cl2F3NO 详情 详情
(IV) 29780 1-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]-1-ethanone C9H7ClF3NO 详情 详情
(V) 29781 1-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]-2-bromo-1-ethanone C9H6BrClF3NO 详情 详情
(VI) 29782 1-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]-2-(tert-butylamino)-1-ethanone C13H16ClF3N2O 详情 详情
Extended Information