2-[4-[4-(3-nitrophenyl)-1-piperazinyl]butyl]tetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione -Drug Synthesis Database

【结构式】

【分子编号】26726

【品名】2-[4-[4-(3-nitrophenyl)-1-piperazinyl]butyl]tetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione

【CA登记号】

【分子式】C₂₀H₂₇N₅O₄

【分子量】401.46568

【元素组成】C 59.84% H 6.78% N 17.44% O 15.94%

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：(V)

The condensation of perhydropyrrolo[1,2-c]imidazole-2,7-dione (I) with 1,4-dibromobutane (II) by means of NaH in DMF gives the expected 4-bromobutyl derivative (III), which is condensed with 1-(3-nitrophenyl)piperazine (IV) by means of triethylamine in hot acetonitrile yielding 2-[4-[4-(3-nitrophenyl)piperazin-1-yl]butyl]perhydropyrrolo[1,2-c]imidazole-2,7-dione (V). The reduction of the nitro group of (V) with H2 over Pd/C in methanol affords the corresponding amino derivative (VI), which is finally sulfonated with ethanesulfonyl chloride and pyridine in acetone.

参考文献中间体

合成目标

【1】 López-Rodríguez, M.L.; et al.; Design and synthesis of 2-[4-[4-(m-(ethylsulfonamido)-penhyl)piperazin-1-yl]butyl]-1,3-dioxoperhydropyrrolo[1,2-c]imidazole (EF-7412) using neural networks. A selective derivative with mixed 5-HT1A/D2 antagonist properties. Bioorg Med Chem Lett 1999, 9, 12, 1679.

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)	25216	tetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione		C₆H₈N₂O₂	详情	详情
(II)	11883	1,4-Dibromobutane; 1,4-Butylene bromide	110-52-1	C₄H₈Br₂	详情	详情
(III)	26724	2-(4-bromobutyl)tetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione		C₁₀H₁₅BrN₂O₂	详情	详情
(IV)	26725	1-(3-nitrophenyl)piperazine		C₁₀H₁₃N₃O₂	详情	详情
(V)	26726	2-[4-[4-(3-nitrophenyl)-1-piperazinyl]butyl]tetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione		C₂₀H₂₇N₅O₄	详情	详情
(VI)	26727	2-[4-[4-(3-aminophenyl)-1-piperazinyl]butyl]tetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione		C₂₀H₂₉N₅O₂	详情	详情

Extended Information