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【结 构 式】

【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%

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:(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
Extended Information