N-(2,5-dichloropentyl)-2-methoxy-5-[methyl(methylsulfonyl)amino]benzamide -Drug Synthesis Database

【结构式】

【分子编号】27334

【品名】N-(2,5-dichloropentyl)-2-methoxy-5-[methyl(methylsulfonyl)amino]benzamide

【CA登记号】

【分子式】C₁₅H₂₂Cl₂N₂O₄S

【分子量】397.32216

【元素组成】C 45.34% H 5.58% Cl 17.85% N 7.05% O 16.11% S 8.07%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(A)

By condensation of 2-aminomethyl-1,4-benzodioxane (I) with 2,6-dimethoxyphenoxyethyl chloride (II) performed by heating at 160 C or by means of K2CO3 in refluxing CHCl3 - water. The starting products (I) and (II) are prepared as follows: 1) The reaction of 2-chloromethyl-1,4-benzodioxane (III) with potassium phthalimide (IV) in refluxing DMF gives 2-phthalimidomethyl-1,4-benzodioxane (V), which is then treated with hydrazine hydrate (A) in refluxing 2-ethoxyethanol to give (I). 2) The condensation of 2,6-dimethoxyphenol (VI) with ethylene carbonate (VII) by means of K2CO3 in refluxing toluene gives 2,6-dimethoxyphenoxyethanol (VIII), which is then refluxed with SOCl2 to afford (II).

参考文献中间体

合成目标

【1】 US 3472874 .
【2】 Castaner, J.; Serradell, M.N.; Hillier, K.; Blancafort, P.; WB-4101. Drugs Fut 1979, 4, 5, 369.
【3】 Green, P.N.; et al.; Synthesis and pharmacological properties of a series of 2-(substituted-aminoethyl)-1,4-benzodioxanes. J Med Chem 1969, 12, 2, 326-329.

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)	27334	N-(2,5-dichloropentyl)-2-methoxy-5-[methyl(methylsulfonyl)amino]benzamide		C₁₅H₂₂Cl₂N₂O₄S	详情	详情
(I)	39477	2,3-dihydro-1,4-benzodioxin-2-ylmethanamine; 2,3-dihydro-1,4-benzodioxin-2-ylmethylamine		C₉H₁₁NO₂	详情	详情
(II)	39479	2-(2-chloroethoxy)-1,3-dimethoxybenzene; 2-(2-chloroethoxy)-3-methoxyphenyl methyl ether		C₁₀H₁₃ClO₃	详情	详情
(III)	39475	2-(chloromethyl)-2,3-dihydro-1,4-benzodioxine	2164-33-2	C₉H₉ClO₂	详情	详情
(IV)	27890	Potassium phthalimide	1074-82-4	C₈H₄KNO₂	详情	详情
(V)	39476	2-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-1H-isoindole-1,3(2H)-dione		C₁₇H₁₃NO₄	详情	详情
(VI)	20228	2,6-dimethoxyphenol	91-10-1	C₈H₁₀O₃	详情	详情
(VII)	32802	1,3-dioxolan-2-one	96-49-1	C₃H₄O₃	详情	详情
(VIII)	39478	2-(2,6-dimethoxyphenoxy)-1-ethanol		C₁₀H₁₄O₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

2-Methoxy-5-(N-methylmethanesulfonamido)-N-tetrahydrofurfurylbenzamide (II), which is prepared from (I) and tetrahydrofurfurylamine, is treated with SOCl2 in dichloroethane to give the dichloro compound (III). Treatment of (III) with EtNH2 gives title compound.

参考文献中间体

合成目标

【1】 Masaru, O.; Hiroshi, M. (Shionogi & Co. Ltd.); Meta-sulfonamido-benzamides. DE 2803651; ES 466366; FR 2378758; GB 1557019; US 4328155; US 4328344; US 4330472; US 4350635; US 4351770; US 44313663 .
【2】 Ogata, M.; 710723-S. Drugs Fut 1985, 10, 9, 758.

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)	27331	2-methoxy-5-[methyl(methylsulfonyl)amino]benzoic acid		C₁₀H₁₃NO₅S	详情	详情
(II)	27333	2-methoxy-5-[methyl(methylsulfonyl)amino]-N-(tetrahydro-3-furanylmethyl)benzamide		C₁₅H₂₂N₂O₅S	详情	详情
(III)	27334	N-(2,5-dichloropentyl)-2-methoxy-5-[methyl(methylsulfonyl)amino]benzamide		C₁₅H₂₂Cl₂N₂O₄S	详情	详情
(IV)	27335	Tetrahydro-2-furanylmethanamine; Tetrahydrofurfurylamine	4795-29-3	C₅H₁₁NO	详情	详情
(V)	10928	Ethanamine	75-04-7	C₂H₇N	详情	详情

Extended Information