3-(1H-imidazol-4-yl)-1-propanamine -Drug Synthesis Database

【结构式】

【分子编号】21507

【品名】3-(1H-imidazol-4-yl)-1-propanamine

【CA登记号】

【分子式】C₆H₁₁N₃

【分子量】125.17356

【元素组成】C 57.57% H 8.86% N 33.57%

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)

The reaction of N-[2-[(5-methyl-4-imidazolyl)methylthio]ethyl]thiourea (I) with methyl iodide in methanol gives the corresponding thiouronium iodide (II), which is converted into the sulfate by treatment with IRA 401 ion-exchange resin. Finally, this sulfate is condensed with 4-(3-aminopropyl)imizadole (III) in refluxing water.

参考文献中间体

合成目标

【1】 Durant, G.J.; et al.; US 4013659 .
【2】 Serradell, M.N.; Hopkins, S.J.; Blancafort, P.; Castaner, J.; Impromidine. Drugs Fut 1979, 4, 9, 647.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	39599	N-(2-[[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl]ethyl)thiourea	C₈H₁₄N₄S₂	详情	详情
(II)	39600	[(2-[[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl]ethyl)amino](methylsulfanyl)methaniminium iodide	C₉H₁₇IN₄S₂	详情	详情
(III)	21507	3-(1H-imidazol-4-yl)-1-propanamine	C₆H₁₁N₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

The acylation of 5-methyl-6-[3-nitro-4-(piperazin-1-yl)phenyl]-4,5-dihydro-3(2H)-pyridazinone (I) with benzoyl isothiocyanate gives the benzoylthiourea (II), which is cleaved by alkaline hydrolysis with potassium carbonate and methylated with methyl iodide to the isothiouronium salt (III). This compound is condensed with 3-(1H-imidazol-4-yl)propylamine (homohistamine, IV) to yield title compound.

参考文献中间体

合成目标

【1】 Herter, R.; Engler, H.; Pfahlert, V.; Weidner, R.; Ahrens, K.H. (Heumann Pharma GmbH & Co.); 6-Oxo-pyridazinderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel. DE 3814057 .
【2】 Morsdorf, P.; Engler, H.; HE 30582. Drugs Fut 1989, 14, 12, 1161.

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)	21504	5-methyl-6-[3-nitro-4-(1-piperazinyl)phenyl]-4,5-dihydro-3(2H)-pyridazinone		C₁₅H₁₉N₅O₃	详情	详情
(II)	21505	N-([4-[4-(4-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridazinyl)-2-nitrophenyl]-1-piperazinyl]carbothioyl)benzamide		C₂₃H₂₄N₆O₄S	详情	详情
(III)	21506	methyl 4-[4-(4-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridazinyl)-2-nitrophenyl]-1-piperazinecarbimidothioate hydroiodide		C₁₇H₂₃IN₆O₃S	详情	详情
(IV)	21507	3-(1H-imidazol-4-yl)-1-propanamine		C₆H₁₁N₃	详情	详情
(V)	23530	benzoyl isothiocyanate	532-55-8	C₈H₅NOS	详情	详情

Extended Information