2-[(2-hydrazinoethyl)amino]-1-ethanol -Drug Synthesis Database

【结构式】

【分子编号】27775

【品名】2-[(2-hydrazinoethyl)amino]-1-ethanol

【CA登记号】

【分子式】C₄H₁₃N₃O

【分子量】119.16684

【元素组成】C 40.32% H 11% N 35.26% O 13.43%

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)

Treatment of 1,4-dichloro-5,8-dihydroxy-9,10-anthracenedione (I) with K2CO3 and benzyl bromide gives the benzyl ether (II) in refluxing acetone, which, followed by treatment with 2-[(2-hydrazinoethyl)amino]ethanol in anhydrous Me2SO, gives product (III). Treatment of product (III) with excess [(2-aminoethyl)amino]methane in refluxing pyridine gives the «two armed» compound, which, followed by treatment with Pearlman's catalyst in glacial AcOH, gives the target compound CI-937.

参考文献中间体

合成目标

【1】 Proc Amer Assoc Cancer Res 1984, 25, 1, 352.
【2】 Hoshi, A.; CI-937 and CI-942. Drugs Fut 1986, 11, 3, 179.
【3】 Showalter, H.D.H.; Johnson, J.L.; Werbel, L.M.; Leopold, W.R.; Jackson, R.C.; Elslager, E.F.; 5-[(Aminoalkyl)amino]-substituted anthra[1, 9-cd]pyrazol-6(2H)-ones as novel anticancer agents. Synthesis and biological evaluation. J Med Chem 1984, 27, 3, 253-5.

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)	27775	2-[(2-hydrazinoethyl)amino]-1-ethanol		C₄H₁₃N₃O	详情	详情
(B)	27777	N-(2-aminoethyl)-N-methylamine	109-81-9	C₃H₁₀N₂	详情	详情
(I)	27773	1,4-dichloro-5,8-dihydroxyanthra-9,10-quinone		C₁₄H₆Cl₂O₄	详情	详情
(II)	27774	1,4-bis(benzyloxy)-5,8-dichloroanthra-9,10-quinone		C₂₈H₁₈Cl₂O₄	详情	详情
(III)	27776	7,10-bis(benzyloxy)-5-chloro-2-[2-[(2-hydroxyethyl)amino]ethyl]dibenzo[cd,g]indazol-6(2H)-one		C₃₂H₂₈ClN₃O₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：

1,4-Dichloro-5-hydroxy-9,10-anthracenedione (I) is alkylated with powdered potassium carbonate and benzyl bromide to give the ether (II). The ether is condensed with threee equivalents of 2-[(2-hydrazinoethyl)amino]ethanol in anhydrous dimethylsulfoxide to give regioisomers (III) and (IV), which are separated by flash silica gel chromatography. The isomer (III) is reacted with an excess of 2-[(2-aminoethyl)amino]ethanol in refluxing pyridine to give the intermediate (V). The intermediate is converted to the 10-hydroxy isomer by hydrogenolysis of the benzyl protecting group with Pearlman's catalyst in glacial acetic acid, followed by dihydrochloride salt formation.

参考文献中间体

合成目标

【1】 Showalter, H.D.H.; Werbel, L.M.; Johnson, J.L.; Elslager, E.F. (Warner-Lambert Co.); Substituted anthra[1,9-cd]pyrazol-6(2H)-ones. EP 0103381 .
【2】 Eastland, G. Jr.; BIANTRAZOLE. Drugs Fut 1989, 14, 8, 742.
【3】 Showalter, H.D.H.; Johnson, J.L.; Werbel, L.M.; Leopold, W.R.; Jackson, R.C.; Elslager, E.F.; 5-[(Aminoalkyl)amino]-substituted anthra[1, 9-cd]pyrazol-6(2H)-ones as novel anticancer agents. Synthesis and biological evaluation. J Med Chem 1984, 27, 3, 253-5.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	12912	1-(Bromomethyl)benzene; Alpha-bromotoluene	100-39-0	C₇H₇Br	详情	详情
	27775	2-[(2-hydrazinoethyl)amino]-1-ethanol		C₄H₁₃N₃O	详情	详情
	32676	2-[(2-aminoethyl)amino]-1-ethanol	111-41-1	C₄H₁₂N₂O	详情	详情
(I)	21210	1,4-dichloro-5-hydroxyanthra-9,10-quinone		C₁₄H₆Cl₂O₃	详情	详情
(II)	21211	5-(benzyloxy)-1,4-dichloroanthra-9,10-quinone		C₂₁H₁₂Cl₂O₃	详情	详情
(III)	21212	7-(benzyloxy)-5-chloro-2-[2-[(2-hydroxyethyl)amino]ethyl]dibenzo[cd,g]indazol-6(2H)-one		C₂₅H₂₂ClN₃O₃	详情	详情
(IV)	21213	10-(benzyloxy)-5-chloro-2-[2-[(2-hydroxyethyl)amino]ethyl]dibenzo[cd,g]indazol-6(2H)-one		C₂₅H₂₂ClN₃O₃	详情	详情
(V)	21214	7-(benzyloxy)-2-[2-[(2-hydroxyethyl)amino]ethyl]-5-([2-[(2-hydroxyethyl)amino]ethyl]amino)dibenzo[cd,g]indazol-6(2H)-one		C₂₉H₃₃N₅O₄	详情	详情

Extended Information