4-bromo-N-{4-[2-(diethylamino)ethoxy]-3-methoxyphenyl}-N-methylbenzamide -Drug Synthesis Database

【结构式】

【分子编号】60901

【品名】4-bromo-N-{4-[2-(diethylamino)ethoxy]-3-methoxyphenyl}-N-methylbenzamide

【CA登记号】

【分子式】C₂₁H₂₇BrN₂O₃

【分子量】435.36106

【元素组成】C 57.94% H 6.25% Br 18.35% N 6.43% O 11.02%

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：(VIII)

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

参考文献中间体

合成目标

【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