2-[[(E)-1-phenyl-2-(1-pyrrolidinyl)ethenyl]imino]malononitrile -Drug Synthesis Database

【结构式】

【分子编号】46510

【品名】2-[[(E)-1-phenyl-2-(1-pyrrolidinyl)ethenyl]imino]malononitrile

【CA登记号】

【分子式】C₁₅H₁₄N₄

【分子量】250.30312

【元素组成】C 71.98% H 5.64% N 22.38%

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：(XXIII)

In an alternative synthesis, phenylacetaldehyde (XVIII) was condensed with pyrrolidine (XIX) to give enamine (XX). Nitrosation of malononitrile (XXI), followed by treatment with tosyl chloride, produced the O-tosyl oxime (XXII). This was condensed with enamine (XX), and to the intermediate adduct (XXIII) was added thiophenol producing the phenylthiopyrazine (XXIV). Subsequent oxidation of the sulfide group of (XXIV) to sulfone (XXV), followed by condensation with methyl thioglycolate, gave the desired thienopyrazine (XIII).

参考文献中间体

合成目标

【1】 Meyer, M.D.; Altenbach, R.J.; Basha, F.; Carroll, W.A.; Drizin, I.; Kerwin, J.F.; Wendt, M.D.; Haight, A.R.; Zhang, W. (Abbott Laboratories Inc.); Benzopyranopyrrole and benzopyranopyridine alpha-1 adrenergic cpds.. EP 0942911; US 5891882; US 6046207; WO 9824791 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XIII)	46503	methyl 7-amino-2-phenylthieno[2,3-b]pyrazine-6-carboxylate		C₁₄H₁₁N₃O₂S	详情	详情
(XVIII)	18456	2-phenylacetaldehyde	122-78-1	C₈H₈O	详情	详情
(XIX)	11376	Pyrrolidine	123-75-1	C₄H₉N	详情	详情
(XX)	46508	1-[(E)-2-phenylethenyl]pyrrolidine		C₁₂H₁₅N	详情	详情
(XXI)	12061	Malononitrile	109-77-3	C₃H₂N₂	详情	详情
(XXII)	46509	2-([[(4-methylphenyl)sulfonyl]oxy]imino)malononitrile		C₁₀H₇N₃O₃S	详情	详情
(XXIII)	46510	2-[[(E)-1-phenyl-2-(1-pyrrolidinyl)ethenyl]imino]malononitrile		C₁₅H₁₄N₄	详情	详情
(XXIV)	46511	6-phenyl-3-(phenylsulfanyl)-2-pyrazinecarbonitrile		C₁₇H₁₁N₃S	详情	详情
(XXV)	46512	6-phenyl-3-(phenylsulfonyl)-2-pyrazinecarbonitrile		C₁₇H₁₁N₃O₂S	详情	详情

Extended Information