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

【结构式】

【分子编号】25216

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

【CA登记号】

【分子式】C₆H₈N₂O₂

【分子量】140.1418

【元素组成】C 51.42% H 5.75% N 19.99% O 22.83%

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：(II)

Perhydropyrrolo[1,2-c]imidazole-1,3-dione (II) was prepared by Urech synthesis upon condensation of proline (I) with potassium cyanate, followed by acid cyclization. Subsequent alkylation of (II) with 1-bromo-4-chlorobutane (III) in the presence of NaH in DMF provided the chlorobutyl derivative (IV). This was finally coupled with aryl piperazine (V) to yield the title compound.

参考文献中间体

合成目标

【1】 Lopez Rodriguez, M.L.; Rosado Samitier, M.L.; Benahmu Salama, B.; Fernandez Velando, E.; Morcillo Ortega, M.J. (Universidad Complutense de Madrid); New arylpiperazine derivs.. ES 2095811; WO 9606846 .

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)	16731	L-proline	147-85-3	C₅H₉NO₂	详情	详情
(II)	25216	tetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione		C₆H₈N₂O₂	详情	详情
(III)	16141	1-bromo-4-chlorobutane	6940-78-9	C₄H₈BrCl	详情	详情
(IV)	25217	2-(4-chlorobutyl)tetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione		C₁₀H₁₅ClN₂O₂	详情	详情
(V)	25218	N-[3-(1-piperazinyl)phenyl]-1-ethanesulfonamide		C₁₂H₁₉N₃O₂S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

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