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【结 构 式】 
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【分子编号】55393 【品名】2-oxo-1-propanesulfenyl cyanide 【CA登记号】 |
【 分 子 式 】C4H5NOS 【 分 子 量 】115.15584 【元素组成】C 41.72% H 4.38% N 12.16% O 13.89% S 27.85% |
合成路线1
该中间体在本合成路线中的序号：(VII)The condensation of 2-(4-bromophenyl)acetic acid methyl ester (I) with 2-(trimethylstannyl)pyridine (II) by means of Pd(PPh3)4 in refluxing toluene gives 2-[4-(2-pyridyl)phenyl]acetic acid methyl ester (III), which is hydrolyzed with KOH in THF/water to yield the corresponding acetic acid (IV). Finally, this compound is condensed with 4-methyl-2-(methylamino)thiazole-5-sulfonamide (V) by means of HOBt and DEC in DMF to afford the target phenylacetamide. The intermediate 4-methyl-2-(methylamino)thiazole-5-sulfonamide (V) is obtained as follows: the reaction of 1-chloroacetone (VI) with KSCN in water gives the corresponding thiocyanato (VII), which is cyclized by means of dry HCl in dichloromethane to yield 2-chloro-4-methylthiazole (VIII). The reaction of (VIII) with Cl-SO3H and SOCl2 affords the sulfonyl chloride (IX), which is treated with ammonia in THF/water to provide 2-chloro-4-methylthiazole-5-sulfonamide (X). Finally, this compound is treated with methylamine in acetonitrile to obtain the target sulfonamide intermediate (V).
| 【1】 Fischer, R.; Bender, W.; Henninger, K.; Eckenberg, P.; Handke, G.; Keldenich, J.; Weber, O.; Kleymann, G.; Betz, U.; Hendrix, M.; Schneider, U.; Jensen, A.; Baumeister, J. (Bayer AG); Thiazolyl amide derivs.. DE 19962532; WO 0147904 . |
| 【2】 Fischer, R.; Bender, W.; Henninger, K.; Eckenberg, P.; Handke, G.; Keldenich, J.; Weber, O.; Kleymann, G.; Betz, U.; Hendrix, M.; Schneider, U.; Jensen, A.; Baumeister, J.; Hewlett, G.; Pevzner, V. (Bayer AG); Incompetitive inhibitors of helicase primase. DE 10044353; WO 0220014 . |
| 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) | 16992 | methyl 2-(4-bromophenyl)acetate | 41841-16-1 | C9H9BrO2 | 详情 | 详情 |
| (II) | 55389 | 2-Pyridyltrimethyltin; Trimethyl(2-pyridyl)tin | 13737-05-8 | C8H13NSn | 详情 | 详情 |
| (III) | 55390 | methyl 2-[4-(2-pyridinyl)phenyl]acetate | C14H13NO2 | 详情 | 详情 | |
| (IV) | 55391 | 2-[4-(2-pyridinyl)phenyl]acetic acid | C13H11NO2 | 详情 | 详情 | |
| (V) | 55392 | 4-methyl-2-(methylamino)-1,3-thiazole-5-sulfonamide | C5H9N3O2S2 | 详情 | 详情 | |
| (VI) | 15288 | 1-Chloroacetone; Chloroacetone | 78-95-5 | C3H5ClO | 详情 | 详情 |
| (VII) | 55393 | 2-oxo-1-propanesulfenyl cyanide | C4H5NOS | 详情 | 详情 | |
| (VIII) | 55394 | 2-chloro-4-methyl-1,3-thiazole | C4H4ClNS | 详情 | 详情 | |
| (IX) | 55395 | 2-chloro-4-methyl-1,3-thiazole-5-sulfonyl chloride | C4H3Cl2NO2S2 | 详情 | 详情 | |
| (X) | 55396 | 2-chloro-4-methyl-1,3-thiazole-5-sulfonamide | C4H5ClN2O2S2 | 详情 | 详情 |