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【结 构 式】 
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【药物名称】PNU-176798 【化学名称】N-[3-[4-(5-Cyanothiazol-2-yl)-3-fluorophenyl]-2-oxooxazolidin-5(S)-ylmethyl]acetamide 【CA登记号】 【 分 子 式 】C16H13FN4O3S 【 分 子 量 】360.36941 |
【开发单位】Pfizer (Originator) 【药理作用】Antibacterial Drugs, ANTIINFECTIVE THERAPY, Oxazolidinones |
合成路线1
Nitrile (II) was prepared from the known amine (I) by diazotization, followed by cyanation with KCN and CuCN. Addition of H2S to (II) in the presence of Et3N in DMF afforded the thioamide (III), which was condensed with chloromalonaldehyde (IV) to produce thiazole (V). Reaction of the formyl group of (V) with hydroxylamine and sodium formate then yielded the target nitrile.
| 【1】 Genin, M.J.; Grega, K.C.; Ford, C.W.; Barbachyn, M.R.; Walker, E.A.; Gadwood, R.C.; Thomasco, L.M.; Zurenko, G.E.; Synthesis and antibacterial activity of azolylphenyl oxazolidinones having carbon-bound 1,3-thiazolyl rings. 38th Intersci Conf Antimicrob Agents Chemother (Sept 24 1998, San Diego) 1998, Abst F-139. |
| 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) | 28504 | N-[[(5S)-3-(4-amino-3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide | C12H14FN3O3 | 详情 | 详情 | |
| (II) | 28555 | N-[[(5S)-3-(4-cyano-3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide | C13H12FN3O3 | 详情 | 详情 | |
| (III) | 28556 | N-([(5S)-3-[4-(aminocarbothioyl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl)acetamide | C13H14FN3O3S | 详情 | 详情 | |
| (IV) | 28557 | 2-chloromalonaldehyde | 36437-19-1 | C3H3ClO2 | 详情 | 详情 |
| (V) | 28558 | N-([(5S)-3-[3-fluoro-4-(5-formyl-1,3-thiazol-2-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl)acetamide | C16H14FN3O4S | 详情 | 详情 |
Extended Information