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【结 构 式】 
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【分子编号】40922 【品名】N,N'-dicyclohexylurea 【CA登记号】2387-23-7 |
【 分 子 式 】C13H24N2O 【 分 子 量 】224.34644 【元素组成】C 69.6% H 10.78% N 12.49% O 7.13% |
合成路线1
该中间体在本合成路线中的序号：The reaction of 5-(2-chlorophenyl)-7-nitro-3H-1,4-benzodiazepin-2-thione (I) with glycine (A) by means of Na2CO3 in refluxing ethanol-water gives 2-carboxymethylamino-7-nitro-5-(2-chlorophenyl)-3H-1,4-benzodiazepine (II), which is cyclized by means of dicyclohexylcarbodiimide in methylene chloride to afford 8-nitro-(2-chlorophenyl)-1,2-dihydro-1H,4H-imidazo[1,2-a][1,4]benzodiazepin-1-one (III). The reaction of (III) with dimethylformamide diethylacetal (B) by means of triethylamine in benzene yields 8-nitro-2-(dimethylaminomethylene)-6-(2-chlorophenyl)-1,2-dihydro-1H,4H-imidazo[1,2a][1,4]benzodiazepin-1-one (IV), which is treated with N-methylpiperazine (C) in refluxing toluene to produce 8-nitro-(2-chlorophenyl)-2-(N-methylpiperazin-1-ylmethylene)-1,2-dihydro-1H,4H-imidazo [1,2-a][1,4]benzodiazepin-1-one (V). This compound is finally treated with methanesulfonic acid.
| 【1】 Taylor, J.B.; Harrison D.R.; 1,2-Dihydro-6-phenyl-1H,4H-imidazobenzodiazepin-1-ones. US 4044142 . |
| 【2】 Ager, J.R.; et al.; Central nervous system activity of a novel class of annelated 1,4-benzodiazwpines, aminomethylene-2,4-dihydro-1H-imidazo[1,2-a][1,4]benzodiazepin-1-ones. J Med Chem 1977, 20, 8, 1035-41. |
| 【3】 Thorpe, P.J.; Castaner, J.; Blancafort, P.; Serradell, M.N.; RU-31,158. Drugs Fut 1980, 5, 3, 144. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 40922 | N,N'-dicyclohexylurea | 2387-23-7 | C13H24N2O | 详情 | 详情 | |
| (A) | 20436 | glycine | 56-40-6 | C2H5NO2 | 详情 | 详情 |
| (B) | 31457 | N-(diethoxymethyl)-N,N-dimethylamine; diethoxy-N,N-dimethylmethanamine | 1188-33-6 | C7H17NO2 | 详情 | 详情 |
| (I) | 32632 | 5-(2-chlorophenyl)-7-nitro-1,3-dihydro-2H-1,4-benzodiazepine-2-thione | C15H10ClN3O2S | 详情 | 详情 | |
| (II) | 32633 | 2-[[5-(2-chlorophenyl)-7-nitro-3H-1,4-benzodiazepin-2-yl]amino]acetic acid | C17H13ClN4O4 | 详情 | 详情 | |
| (III) | 30373 | 6-(2-chlorophenyl)-8-nitro-2,4-dihydro-1H-imidazo[1,2-a][1,4]benzodiazepin-1-one | C17H11ClN4O3 | 详情 | 详情 | |
| (IV) | 32634 | 6-(2-chlorophenyl)-2-[(Z)-(dimethylamino)methylidene]-8-nitro-1H-imidazo[1,2-a][1,4]benzodiazepin-1(4H)-one | C20H16ClN5O3 | 详情 | 详情 | |
| (V) | 30375 | 6-(2-chlorophenyl)-2-[(Z)-(4-methyl-1-piperazinyl)methylidene]-8-nitro-1H-imidazo[1,2-a][1,4]benzodiazepin-1(4H)-one | C23H21ClN6O3 | 详情 | 详情 | |
| (C) | 10061 | 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine | 109-01-3 | C5H12N2 | 详情 | 详情 |