N-(5-amino-2-[2-[(3,4-dimethoxyphenethyl)(methyl)amino]ethoxy]phenyl)acetamide -Drug Synthesis Database

【结构式】

【分子编号】19886

【品名】N-(5-amino-2-[2-[(3,4-dimethoxyphenethyl)(methyl)amino]ethoxy]phenyl)acetamide

【CA登记号】

【分子式】C₂₁H₂₉N₃O₄

【分子量】387.47908

【元素组成】C 65.1% H 7.54% N 10.84% O 16.52%

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：(VI)

Alkylation of phenol (I) with 1,2-dibromoethane (II) in the presence of K2CO3 in DMF yielded bromoethyl ether (III), which was further, condensed with amine (IV) to afford tertiary amine (V). The nitro group of (V) was then reduced by either catalytic hydrogenation in the presence of Pd/C or by treatment with SnCl2 in aqueous HCl, and the resulting aniline (VI) was condensed with methanesulfonyl chloride in pyridine to give sulfonamide (VII). Finally, acid hydrolysis of the acetamido group provided the title compound.

参考文献中间体

合成目标

【1】 Kim, D.-I.; Kim, H.Y.; Kwon, L.S.; Park, S.D.; Jeon, G.H.; Jung, K.Y.; Min, J.K.; Nam, W.H.; Lee, K.; Chung, Y.S.; Tanabe, S.; Kozono, T.; Synthesis and biological activity of KCB-328 and its analogues: Novel class III antiarrhythmic agents with little reverse frequency dependence. Bioorg Med Chem Lett 1999, 9, 1, 85.

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)	19881	N-(2-hydroxy-5-nitrophenyl)acetamide		C₈H₈N₂O₄	详情	详情
(II)	10252	1,2-Dibromoethane; Ethylene dibromide	106-93-4	C₂H₄Br₂	详情	详情
(III)	18938	2-(3,4-dimethoxyphenyl)-N-methyl-1-ethanamine; N-(3,4-dimethoxyphenethyl)-N-methylamine	3490-06-0	C₁₁H₁₇NO₂	详情	详情
(III)	19883	N-[2-(2-bromoethoxy)-5-nitrophenyl]acetamide		C₁₀H₁₁BrN₂O₄	详情	详情
(V)	19885	N-(2-[2-[(3,4-dimethoxyphenethyl)(methyl)amino]ethoxy]-5-nitrophenyl)acetamide		C₂₁H₂₇N₃O₆	详情	详情
(VI)	19886	N-(5-amino-2-[2-[(3,4-dimethoxyphenethyl)(methyl)amino]ethoxy]phenyl)acetamide		C₂₁H₂₉N₃O₄	详情	详情
(VII)	19887	N-[2-[2-[(3,4-dimethoxyphenethyl)(methyl)amino]ethoxy]-5-[(methylsulfonyl)amino]phenyl]acetamide		C₂₂H₃₁N₃O₆S	详情	详情

Extended Information