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【结 构 式】 
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【分子编号】20396 【品名】3-[(2-chloro-4-nitrophenoxy)methyl]-N,N-dimethylbenzamide 【CA登记号】 |
【 分 子 式 】C16H15ClN2O4 【 分 子 量 】334.75888 【元素组成】C 57.41% H 4.52% Cl 10.59% N 8.37% O 19.12% |
合成路线1
该中间体在本合成路线中的序号：(VI)The key intermediate alpha-(2-chloro-4-nitrophenoxy)-m-toluic acid (IV) is prepared from methyl m-toluate (I) by bromination with N-bromosuccinimide in the presence of benzoyl peroxide, then condensation with 2-chloro-4-nitrophenol, followed by basic hydrolysis. The carboxylic acid group of compound (IV) is converted to dimethylamide (VI) via acyl chloride (V). The nitro intermediate (VI) is hydrogenated over platinum oxide in 2-methoxyethanol. The resulting amine (VII) is then condensed with cyanoguanidine and acetone in the presence of ethanesulfonic acid to give triazinate.
| 【1】 Baker, B.R.; Ashton, W.T.; Irreversible enzyme inhibitors. CLXXIX. Active-site-directed irreversible enzyme inhibitors of dihydrofolate reductase from 1-(3-chlorophenyl)-4, 6-diamino-1,2-dihydro-2,2-dimethyl-s-triazine with oxyamine bridges to a terminal sulfonyl flouride. J Med Chem 1970, 13, 1165-70. |
| 【2】 Chang, P.; TRIAZINATE. Drugs Fut 1989, 14, 2, 138. |
| 【3】 Baker, B.R.; Ashton, W.T.; Water-soluble reversible inhibitors of dihydrofolate reductase with potent antitumor activity derived from 4,6-diamino-1,2-dihydro-2, 2-dimethyl-1-phenyl-s-triazine. J Med Chem 1973, 16, 209-14. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 23611 | N-cyanoguanidine | 461-58-5 | C2H4N4 | 详情 | 详情 | |
| 49872 | 1-Chloro-2-Hydroxy-5-Nitrobenzene; 2-Chloro-4-nitrophenol; 4-Nitro-2-chlorophenol; p-Nitro-o-chlorophenol | 619-08-9 | C6H4ClNO3 | 详情 | 详情 | |
| (I) | 20391 | methyl 3-methylbenzoate | 99-36-5 | C9H10O2 | 详情 | 详情 |
| (II) | 20392 | methyl 3-(bromomethyl)benzoate | 1129-28-8 | C9H9BrO2 | 详情 | 详情 |
| (III) | 20393 | methyl 3-[(2-chloro-4-nitrophenoxy)methyl]benzoate | C15H12ClNO5 | 详情 | 详情 | |
| (IV) | 20394 | 3-[(2-chloro-4-nitrophenoxy)methyl]benzoic acid | C14H10ClNO5 | 详情 | 详情 | |
| (V) | 20395 | 3-[(2-chloro-4-nitrophenoxy)methyl]benzoyl chloride | C14H9Cl2NO4 | 详情 | 详情 | |
| (VI) | 20396 | 3-[(2-chloro-4-nitrophenoxy)methyl]-N,N-dimethylbenzamide | C16H15ClN2O4 | 详情 | 详情 | |
| (VII) | 20397 | 3-[(4-amino-2-chlorophenoxy)methyl]-N,N-dimethylbenzamide | C16H17ClN2O2 | 详情 | 详情 |