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【结 构 式】

【分子编号】16140

【品名】1-[[(E)-benzylidene]amino]-1H-imidazole-2,4(3H,5H)-dione

【CA登记号】

【 分 子 式 】C10H9N3O2

【 分 子 量 】203.20048

【元素组成】C 59.11% H 4.46% N 20.68% O 15.75%

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:(I)

The condensation of 1-(benzylideneamino)imidazolidine-2,4-dione (I) with 1-bromo-4-chlorobutane (II) by means of NaH in DMF at 100 C yields 1-(benzylideneamino)-3-(4-chlorobutyl)imidazolidine-2,4-dione (III), which is treated with NaI in refluxing acetone affording the corresponding 4-iodobutyl derivative (IV). The thermal condensation of (IV) with 1-methylpiperazine (V) in refluxing DMF gives the expected condensation product (VI), which is debenzylated by hydrogenation with H2 over Pd/C in 2N HCl giving 1-amino-3-[4-(4-methylpiperazin-1-yl)butyl]imidazolidine-2,4-dione (VII). Finally, this compound is condensed with 5-(4-chlorophenyl)furan-2-carbaldehyde (VIII) in DMF at room temperature.

1 Robinson, C.P.; Robinson, K.A.; Castaner, J.; Azimilide Hydrochloride. Drugs Fut 1997, 22, 6, 601.
2 Pelosi, S.S. Jr.; Yu, C.-NN.; Calcagno, M.A. (The Procter & Gamble Co.); Novel 4-oxocyclic ureas useful as antiarrhythmic and antifibrillatory agents. EP 0598061; JP 1994509804; US 5462940; WO 9304061 .
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) 16140 1-[[(E)-benzylidene]amino]-1H-imidazole-2,4(3H,5H)-dione C10H9N3O2 详情 详情
(II) 16141 1-bromo-4-chlorobutane 6940-78-9 C4H8BrCl 详情 详情
(III) 16142 3-(4-chlorobutyl)-1-[[(E)-benzylidene]amino]-1H-imidazole-2,4(3H,5H)-dione C14H16ClN3O2 详情 详情
(IV) 16143 3-(4-iodobutyl)-1-[[(E)-benzylidene]amino]-1H-imidazole-2,4(3H,5H)-dione C14H16IN3O2 详情 详情
(V) 10061 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine 109-01-3 C5H12N2 详情 详情
(VI) 16145 3-[4-(4-methylpiperazino)butyl]-1-[[(E)-benzylidene]amino]-1H-imidazole-2,4(3H,5H)-dione C19H27N5O2 详情 详情
(VII) 16146 1-amino-3-[4-(4-methylpiperazino)butyl]-1H-imidazole-2,4(3H,5H)-dione C12H23N5O2 详情 详情
(VIII) 16147 5-(4-Chloro-phenyl)-furan-2-carbaldehyde; 5-(4-Chlorophenyl)-2-furaldehyde 34035-03-5 C11H7ClO2 详情 详情
Extended Information