4-(aminomethyl)-1-[[2-(diethylamino)ethyl]amino]-9H-thioxanthen-9-one -Drug Synthesis Database

【结构式】

【分子编号】27506

【品名】4-(aminomethyl)-1-[[2-(diethylamino)ethyl]amino]-9H-thioxanthen-9-one

【CA登记号】

【分子式】C₂₀H₂₅N₃OS

【分子量】355.50412

【元素组成】C 67.57% H 7.09% N 11.82% O 4.5% S 9.02%

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：(III)

Leuckart reaction of aldehyde (I) with formamide/formic acid at 160 C provided formamide derivative (II), which was hydrolyzed with refluxing 2N HCl to afford benzylic amine (III). Finally, treatment with methanesulfonyl chloride, in the presence of NEt3 yielded the title sulfonamide.

参考文献中间体

合成目标

【1】 Perni, R.B.; Wentland, M.P.; Huang, J.I.; Powles, R.G.; Aldous, S.; Klingbeil, K.M.; Peverly, A.D.; Robinson, R.G.; Corbett, T.H.; Jones, J.L.; Mattes, K.C.; Rake, J.B.; Coughlin, S.A.; Synthesis and antitumor activity of 4-aminomethylthioxanthenone and 5-aminomethylbenzothiopyranoindazole derivatives. J Med Chem 1998, 41, 19, 3645.
【2】 Wentland, M.P.; et al.; Anti-solid tumor efficacy and preparation of N-[[1-[[2-(diethylamino)ethyl]amino]-9-oxo-9H-thioxanthen-4-yl]methyl]methanesulfonamide (WIN 33377) and related derivatives. Bioorg Med Chem Lett 1994, 4, 4, 609.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	27504	1-[[2-(diethylamino)ethyl]amino]-9-oxo-9H-thioxanthene-4-carbaldehyde	C₂₀H₂₂N₂O₂S	详情	详情
(II)	27505	(1-[[2-(diethylamino)ethyl]amino]-9-oxo-9H-thioxanthen-4-yl)methylformamide	C₂₁H₂₅N₃O₂S	详情	详情
(III)	27506	4-(aminomethyl)-1-[[2-(diethylamino)ethyl]amino]-9H-thioxanthen-9-one	C₂₀H₂₅N₃OS	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

The reaction of 1-[2-(diethylamino)ethylamino]-9-oxothioxanthene-4-carbaldehyde (I) with formic acid and formamide at 160 C gives N-[1-[2-(diethylamino)ethylamino]-9-oxothioxanthen-4-ylmethyl]formamide (II), which is hydrolyzed with hot aqueous HCl yielding the corresponding amine (III). Finally, this compound is acylated with methyl chloroformate and TEA in dichloromethane.

参考文献中间体

合成目标

【1】 Brown, S.; Sandhu, G.S. (Sanofi-Synthelabo); Lyophilized thioxanthenone antitumor agents. WO 9710809 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	16993	methyl chlorocarbonate;Carbonochloridic acid methyl ester；[(chlorocarbonyl)oxy]methane；methyl chloroformate	79-22-1	C₂H₃ClO₂	详情	详情
(I)	27504	1-[[2-(diethylamino)ethyl]amino]-9-oxo-9H-thioxanthene-4-carbaldehyde		C₂₀H₂₂N₂O₂S	详情	详情
(II)	27505	(1-[[2-(diethylamino)ethyl]amino]-9-oxo-9H-thioxanthen-4-yl)methylformamide		C₂₁H₂₅N₃O₂S	详情	详情
(III)	27506	4-(aminomethyl)-1-[[2-(diethylamino)ethyl]amino]-9H-thioxanthen-9-one		C₂₀H₂₅N₃OS	详情	详情

Extended Information