(E)-N’-(3,7-dimethylocta-2,6-dienyl)ethane-1,2-diamine -Drug Synthesis Database

【结构式】

【分子编号】66063

【品名】(E)-N’-(3,7-dimethylocta-2,6-dienyl)ethane-1,2-diamine

【CA登记号】　

【分子式】C₁₂H₂₄N₂

【分子量】196.33604

【元素组成】C 73.41% H 12.32% N 14.27%

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：(X)

In an adapted method, complete solution-phase synthesis of SQ-109 is achieved by the substitution of (2E)-1-bromo-3,7-dimethylocta-2,6-diene (VIII) by ethylene diamine (IX) at –78 °C in dry DCM to give (E)-N’-(3,7-dimethylocta-2,6-dienyl)ethane-1,2-diamine (X) (4, 5). Finally, amine (X) is made to undergo reductive amination with 2-adamantanone (XI) in MeOH using NaBH4 under an N2 atmosphere overnight to give SQ-109, which can be extracted with ethyl acetate or converted to a hydrochloride salt using HCl and MeOH. Scheme 2.

参考文献中间体

合成目标

【4】 Onajole, O.K., Govender, P., van Helden, P.D., Kruger, H.G., Maguire, G.E., Wiid, I., Govender, T. Synthesis and evaluation of SQ109 analogues as potential anti-tuberculosis candidates. Eur J Med Chem 2010, 45(5): 2075-9.
【5】 Onajole, O.K., Sosibo, S., Govender, P. et al. Novel linear diamine disubstituted polycyclic ‘cage’ derivatives as potential antimycobacterial candidates. Chem Biol Drug Design 2011, 78(6): 1022-30.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VIII)	31116	(2E)-1-bromo-3,7-dimethyl-2,6-octadiene; trans-Geranyl bromide; Geranyl bromide	6138-90-5	C₁₀H₁₇Br	详情	详情
(IX)	14754	ethylenediamine;1,2-Diaminoethane;ethane-1,2-diamine；1,2-Ethanediamine	107-15-3	C₂H₈N₂	详情	详情
(X)	66063	(E)-N’-(3,7-dimethylocta-2,6-dienyl)ethane-1,2-diamine		C₁₂H₂₄N₂	详情	详情
(XI)	40404	2-adamantanone	700-58-3	C₁₀H₁₄O	详情	详情

Extended Information