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【结 构 式】 
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【分子编号】12103 【品名】N-[2-Bromo-5-(trifluoromethyl)phenyl]ethanethioamide 【CA登记号】 |
【 分 子 式 】C9H7BrF3NS 【 分 子 量 】298.1265296 【元素组成】C 36.26% H 2.37% Br 26.8% F 19.12% N 4.7% S 10.76% |
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：(IX)5) Esterified intermediate (IV) can also be obtained as follows: The reaction of 2-bromo-5-(trifluoromethyl)acetanilide (VIII) with phosphorus pentasulfide in refluxing benzene gives the corresponding thioamide (IX), which is cyclized by means of NaH in hot N-methylpyrrolidone yielding 2-methyl-5-(trifluoromethyl)benzothiazole (X). The bromination of (X) with N-bromosuccinimide (NBS) and benzoyl peroxide in refluxing CCl4 affords the corresponding bromomethyl derivative (XI), which is then condensed with phthalazinone (I) by means of NaH in DMF.
| 【1】 Mealy, N.; Prous, J.; Castaner, J.; Zopolrestat. Drugs Fut 1995, 20, 1, 33. |
| 【2】 Mylari, B.L.; Zembrowski, W.J.; Synthesis of aldose reductase inhibitor, 3,4-dihydro-4-oxo-3-[[5-(trifluoromethyl)-2 14C benzothiazolyl]methyl]-1-phthalazineacetic acid. J Label Compd Radiopharm 1991, 29, 2, 143-8. |
| 【3】 Mylari, B.L.; Larson, E.R.; Zembrowski, W.J. (Pfizer Inc.); Heterocyclic oxophthalazinylacetic acids. EP 0222576; JP 1987114988; US 4939140 . |
| 【4】 Mylari, B.L.; Zembrowski, W.J. (Pfizer Inc.); Preparation of oxophthalazinyl acetic acids having benzothiazole or other heterocyclic side chains. EP 0295051 . |
| 【5】 Siegel, T.W.; Aldinger, C.E.; Mylari, B.L.; Singleton, D.H.; Zembrowski, W.J.; Larson, E.R.; Beyer, T.A.; Dee, M.F.; Novel, potent aldose reductase inhibitors: 3,4-Dihydro-4-oxo-3-[[5-(trifluoromethyl)-2-benzothiazolyl]methyl]-1-phthalazine-acetic acid (zopolrestat) and congeners. J Med Chem 1991, 34, 1, 108-22. |
| 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) | 12095 | ethyl 2-(4-oxo-3,4-dihydro-1-phthalazinyl)acetate; Ethyl 3,4-dihydro-4-oxo-1-phthalazineacetate | 25947-13-1 | C12H12N2O3 | 详情 | 详情 |
| (IV) | 23855 | 2-(4-oxo-3-[[5-(trifluoromethyl)-1,3-benzothiazol-2-yl]methyl]-3,4-dihydro-1-phthalazinyl)acetic acid | C19H12F3N3O3S | 详情 | 详情 | |
| (VIII) | 12102 | N-[2-Bromo-5-(trifluoromethyl)phenyl]acetamide | C9H7BrF3NO | 详情 | 详情 | |
| (IX) | 12103 | N-[2-Bromo-5-(trifluoromethyl)phenyl]ethanethioamide | C9H7BrF3NS | 详情 | 详情 | |
| (X) | 12104 | 2-Methyl-5-(trifluoromethyl)-1,3-benzothiazole | 398-99-2 | C9H6F3NS | 详情 | 详情 |
| (XI) | 12105 | 2-(Bromomethyl)-5-(trifluoromethyl)-1,3-benzothiazole | C9H5BrF3NS | 详情 | 详情 |
Extended Information