N-[4-([1,7-bis[(2-nitrophenyl)sulfonyl]-1,4,7-triazacyclotetradecan-4-yl]methyl)benzyl]-2-nitro-N-(2-pyridinylmethyl)benzenesulfonamide -Drug Synthesis Database

【结构式】

【分子编号】46252

【品名】N-[4-([1,7-bis[(2-nitrophenyl)sulfonyl]-1,4,7-triazacyclotetradecan-4-yl]methyl)benzyl]-2-nitro-N-(2-pyridinylmethyl)benzenesulfonamide

【CA登记号】

【分子式】C₄₃H₄₈N₈O₁₂S₃

【分子量】965.09884

【元素组成】C 53.52% H 5.01% N 11.61% O 19.89% S 9.97%

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)

The acylation of 1,7-heptanediamine (I) with 2-nitrobenzenesulfonyl chloride (II) by means of TEA in dichloromethane gives the bis sulfamide (III), which is submitted to macrocyclization with the dimesylate (IV) by means of Cs2CO3 in hot DMF, yielding the protected 1,4,7-triazacyclotetradecane (V). The cleavage of the phosphoryl group of (IV) with HBr in acetic acid affords the secondary amine (VI), which is alkylated with he benzyl chloride (VII) by means of K2CO3 in refluxing acetonitrile, providing the adduct (VIII). This compound is deprotected with K2CO3 in DMF and treated with HCl or HBr to furnish the corresponding target salts.

参考文献中间体

合成目标

【2】 Bogucki, D.E.; Boehringer, E.M.; Wang, Z.; Bridger, G.J.; Schols, D.; Skerlj, R.T. (AnorMED Inc.); Antiviral macrocyclic cpds.. EP 1095031; WO 0002870 .
【1】 De Clercq, E.; HEnson, G.; Schols, D.; Witvrouw, M.; Macfarland, R.T.; Bridger, G.J.; Skerli, R.T.; Yasuda, N.; An orally bioavailable CXCR4 antagonist for inhibition of HIV replication. 40th Intersci Conf Antimicrob Agents Chemother (Sept 17 2000, Toronto) 2000, Abst F-1845.

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)	12941	7-Aminoheptylamine; 1,7-Diaminoheptane; 1,7-Heptanediamine	646-19-5	C₇H₁₈N₂	详情	详情
(II)	32624	2-Nitrobenzenesulfonyl chloride	1694-92-4	C₆H₄ClNO₄S	详情	详情
(III)	46248	2-nitro-N-(7-[[(2-nitrophenyl)sulfonyl]amino]heptyl)benzenesulfonamide		C₁₉H₂₄N₄O₈S₂	详情	详情
(IV)	34634	2-((diethoxyphosphoryl)[2-[(methylsulfonyl)oxy]ethyl]amino)ethyl methanesulfonate		C₁₀H₂₄NO₉PS₂	详情	详情
(V)	46249	diethyl 1,7-bis[(2-nitrophenyl)sulfonyl]-1,4,7-triazacyclotetradecan-4-ylphosphonate		C₂₇H₄₀N₅O₁₁PS₂	详情	详情
(VI)	46250	1,7-bis[(2-nitrophenyl)sulfonyl]-1,4,7-triazacyclotetradecane		C₂₃H₃₁N₅O₈S₂	详情	详情
(VII)	46251	N-[4-(chloromethyl)benzyl]-2-nitro-N-(2-pyridinylmethyl)benzenesulfonamide		C₂₀H₁₈ClN₃O₄S	详情	详情
(VIII)	46252	N-[4-([1,7-bis[(2-nitrophenyl)sulfonyl]-1,4,7-triazacyclotetradecan-4-yl]methyl)benzyl]-2-nitro-N-(2-pyridinylmethyl)benzenesulfonamide		C₄₃H₄₈N₈O₁₂S₃	详情	详情

Extended Information