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【结 构 式】 
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【分子编号】33263 【品名】[2-[2-(chloromethyl)-1H-imidazol-1-yl]-5-nitrophenyl](2-chlorophenyl)methanone 【CA登记号】 |
【 分 子 式 】C17H11Cl2N3O3 【 分 子 量 】376.19816 【元素组成】C 54.28% H 2.95% Cl 18.85% N 11.17% O 12.76% |
合成路线1
该中间体在本合成路线中的序号：(VI)Compound can be prepared in two different ways: 1) The Sandmeyer reaction of 2-amino-5-nitro-2'-chlorobenzophenone (I) with HCl, NaNO2 and CuCl gives 2,2'-dichloro-5-nitrobenzophenone (II), which is condensed with 2-diethylaminomethylimidazole (III) by means of NaH in DMF to afford the free base of Y-9179 (IV). Finally, this compound is treated with fumaric acid (B). 2) The treatment of 1-[2-(2-chlorobenzoyl)-4-nitrophenyl]-2-hydroxymethyl-imidazole (V) with SOCl2 gives the corresponding 2-chloromethyl derivative (VI), which is then treated with diethylamine (A) and Na2CO3 in benzene-DMF at 60 C.
| 【1】 Nakanishi, M.; et al. (Welfide Corporation); 1-[2-(2-Chlorobenzoyl)-4-nitrophenyl]-2-(diethylaminomethyl)imidazole. US 3915981 . |
| 【2】 Roberts, P.J.; Castaner, J.; Y-9179. Drugs Fut 1979, 4, 2, 148. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (B) | 23808 | Fumaric acid; (E)-2-butenedioic acid | 110-17-8 | C4H4O4 | 详情 | 详情 |
| (A) | 24486 | Diethylamine; N,N-Diethylamine | 109-89-7 | C4H11N | 详情 | 详情 |
| (I) | 33258 | 2-Amino-2'-chloro-5-nitrobenzophenone; (2-Amino-5-nitrophenyl)(2-chlorophenyl)methanone; 2-Amino-5-nitro-2'-chlorobenzophenone | 2011-66-7 | C13H9ClN2O3 | 详情 | 详情 |
| (II) | 33259 | (2-Chloro-5-nitrophenyl)(2-chlorophenyl)methanone; 2,2'-Dichloro-5-nitrobenzophenone | C13H7Cl2NO3 | 详情 | 详情 | |
| (III) | 33260 | N,N-diethyl-N-(1H-imidazol-2-ylmethyl)amine; 2-Diethylaminomethylimidazole; N-ethyl-N-(1H-imidazol-2-ylmethyl)-1-ethanamine | C8H15N3 | 详情 | 详情 | |
| (IV) | 33261 | (2-chlorophenyl)(2-[2-[(diethylamino)methyl]-1H-imidazol-1-yl]-5-nitrophenyl)methanone | C21H21ClN4O3 | 详情 | 详情 | |
| (V) | 33262 | 1-[2-(2-Chlorobenzoyl)-4-nitrophenyl]-2-hydroxymethyl-imidazole; (2-Chlorophenyl)[2-[2-(hydroxymethyl)-1H-imidazol-1-yl]-5-nitrophenyl]methanone | C17H12ClN3O4 | 详情 | 详情 | |
| (VI) | 33263 | [2-[2-(chloromethyl)-1H-imidazol-1-yl]-5-nitrophenyl](2-chlorophenyl)methanone | C17H11Cl2N3O3 | 详情 | 详情 |