N-(4-aminobutyl)-N-ethyl-2,4,6-trimethylbenzenesulfonamide -Drug Synthesis Database

【结构式】

【分子编号】46927

【品名】N-(4-aminobutyl)-N-ethyl-2,4,6-trimethylbenzenesulfonamide

【CA登记号】

【分子式】C₁₅H₂₆N₂O₂S

【分子量】298.44972

【元素组成】C 60.37% H 8.78% N 9.39% O 10.72% S 10.74%

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：(IV)

Alkylation of N-ethyl mesitylenesulfonamide (I) with 4-bromobutyronitrile (II) in the presence of NaH afforded the cyano sulfonamide (III). After catalytic hydrogenation of the cyano group of (III), the resulting amine (IV) was acylated with mesitylenesulfonyl chloride (V) to give the bis-sulfonamide (VI) (1). Subsequent condensation of (VI) with the bis-sulfonate (VII) produced the tetra-sulfonamide (VIII). Finally, cleavage of the mesitylenesulfonyl protecting groups of (VIII) using HBr in HOAc furnished the corresponding tetraamine, which was isolated as the hydrochloride salt.

参考文献中间体

合成目标

【2】 Marton, L.J.; Frydman, B. (SLIL Biomedical Corp.); Novel polyamine analog conjugates and quinone conjugates as therapies for cancers and prostate diseases. WO 0066175 .
【1】 Sarkar, A.; Basu, H.S.; Marton, L.J.; Valasinas, A.; Frydman, B.; Reddy, V.K.; Conformationally restricted analogues of 1N,14N-bisethylhomospermine (BE-4-4-4): Synthesis and growth inhibitory effects on human prostate cancer cells. J Med Chem 2001, 44, 3, 390.

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)	46925	N-ethyl-2,4,6-trimethylbenzenesulfonamide		C₁₁H₁₇NO₂S	详情	详情
(II)	34789	4-bromobutanenitrile	5332-06-9	C₄H₆BrN	详情	详情
(III)	46926	N-(3-cyanopropyl)-N-ethyl-2,4,6-trimethylbenzenesulfonamide		C₁₅H₂₂N₂O₂S	详情	详情
(IV)	46927	N-(4-aminobutyl)-N-ethyl-2,4,6-trimethylbenzenesulfonamide		C₁₅H₂₆N₂O₂S	详情	详情
(V)	41158	2,4,6-trimethylbenzenesulfonyl chloride	773-64-8	C₉H₁₁ClO₂S	详情	详情
(VI)	46928	N-ethyl-N-[4-[(mesitylsulfonyl)amino]butyl]-2,4,6-trimethylbenzenesulfonamide		C₂₄H₃₆N₂O₄S₂	详情	详情
(VII)	46929	((1R,2R)-2-[[(mesitylsulfonyl)oxy]methyl]cyclopropyl)methyl 2,4,6-trimethylbenzenesulfonate		C₂₃H₃₀O₆S₂	详情	详情
(VIII)	46930	N-ethyl-N-[4-[[((1R,2R)-2-[[[4-[ethyl(mesitylsulfonyl)amino]butyl](mesitylsulfonyl)amino]methyl]cyclopropyl)methyl](mesitylsulfonyl)amino]butyl]-2,4,6-trimethylbenzenesulfonamide		C₅₃H₇₈N₄O₈S₄	详情	详情

Extended Information