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【结 构 式】

【分子编号】60899

【品名】ethyl 4-[2-(diethylamino)ethoxy]-3-methoxyphenyliminoformate

【CA登记号】

【 分 子 式 】C16H26N2O3

【 分 子 量 】294.39412

【元素组成】C 65.28% H 8.9% N 9.52% O 16.3%

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)

Substitution of 1-chloro-2-methoxy-4-nitrobenzene (I) with 2-(diethylamino)ethanol (II) gives rise to ether (III). Subsequent nitro group reduction in (III) by catalytic hydrogenation affords aniline (IV). Condensation of amine (IV) with triethyl orthoformate, followed by reduction of the resultant formimidate (V) with NaBH4 leads to the N-methyl amine (VI). This is acylated by 4-bromobenzoyl chloride (VII) to furnish the bromobenzamide (VIII). Finally, Suzuki coupling of bromide (VIII) with 4-trifluoromethylphenylboronic acid (IX) produces the title biphenyl compound

1 Stemp, G.; Johnson, C.N.; Jones, M.; O'Toole, C.A.; Thewlis, K.M.; Witty, D. (GlaxoSmithKline plc); Carboxamide cpds. and their use as antagonists of a human 11CBy receptor. EP 1305304; WO 0210146 .
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) 60896 1-chloro-2-methoxy-4-nitrobenzene; 2-chloro-5-nitrophenyl methyl ether C7H6ClNO3 详情 详情
(II) 16183 Diethylaminoethanol; 2-(diethylamino)-1-ethanol 100-37-8 C6H15NO 详情 详情
(III) 60897 N,N-diethyl-2-(2-methoxy-4-nitrophenoxy)-1-ethanamine; N,N-diethyl-N-[2-(2-methoxy-4-nitrophenoxy)ethyl]amine C13H20N2O4 详情 详情
(IV) 60898 N-[2-(4-amino-2-methoxyphenoxy)ethyl]-N,N-diethylamine; 4-[2-(diethylamino)ethoxy]-3-methoxyaniline C13H22N2O2 详情 详情
(V) 60899 ethyl 4-[2-(diethylamino)ethoxy]-3-methoxyphenyliminoformate C16H26N2O3 详情 详情
(VI) 60900 N-{4-[2-(diethylamino)ethoxy]-3-methoxyphenyl}-N-methylamine; 4-[2-(diethylamino)ethoxy]-3-methoxy-N-methylaniline C14H24N2O2 详情 详情
(VII) 45960 4-bromobenzoyl chloride 586-75-4 C7H4BrClO 详情 详情
(VIII) 60901 4-bromo-N-{4-[2-(diethylamino)ethoxy]-3-methoxyphenyl}-N-methylbenzamide C21H27BrN2O3 详情 详情
(IX) 48639 4-(Trifluoromethyl)phenylboronic acid C7H6BF3O2 详情 详情
Extended Information