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【结 构 式】 
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【分子编号】61914 【品名】benzyl 4-[6-(methylsulfanyl)-3-pyridazinyl]phenylcarbamate 【CA登记号】 |
【 分 子 式 】C19H17N3O2S 【 分 子 量 】351.429 【元素组成】C 64.94% H 4.88% N 11.96% O 9.11% S 9.12% |
合成路线1
该中间体在本合成路线中的序号：(V)The cyclization of 4-(benzyloxycarbonylamino)acetophenone (I) with glyoxylic acid (II) and hydrazine (III) in hot acetic acid gives the pyridazinone (IV), which is treated first with Lawesson's reagent in hot dioxane and then with MeI and TEA in DMF to yield the methylsulfanyl pyridazine (V). The cyclization of (V) with acetamide (VI) by means of t-BuOLi in methanol/DMF affords the oxazolidinone (VII), which is finally treated with Lawesson's reagent in hot dioxane to provide the target thioacetamide.
| 【1】 Luehr, G.W.; Wang, S.; Hackbarth, C.J.; Gomez, M.; Trias, J.; Patel, D.V.; Gordeev, M.F.; Novel antimicrobial pyridazine phenyloxazolidinones. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-1320. |
| 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) | 61912 | benzyl 4-acetylphenylcarbamate | C16H15NO3 | 详情 | 详情 | |
| (II) | 15618 | 2-Oxoacetic acid; Glyoxylic Acid | 298-12-4 | C2H2O3 | 详情 | 详情 |
| (III) | 27344 | hydrazine | 302-01-2 | H4N2 | 详情 | 详情 |
| (IV) | 61913 | benzyl 4-(6-oxo-1,6-dihydro-3-pyridazinyl)phenylcarbamate | C18H15N3O3 | 详情 | 详情 | |
| (V) | 61914 | benzyl 4-[6-(methylsulfanyl)-3-pyridazinyl]phenylcarbamate | C19H17N3O2S | 详情 | 详情 | |
| (VI) | 61915 | (1S)-2-(acetylamino)-1-(chloromethyl)ethyl acetate | C7H12ClNO3 | 详情 | 详情 | |
| (VII) | 61916 | N-[((5S)-3-{4-[6-(methylsulfanyl)-3-pyridazinyl]phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide | C17H18N4O3S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(V)The cyclization of 4-(benzyloxycarbonylamino)acetophenone (I) with glyoxylic acid (II) and hydrazine (III) in hot acetic acid gives the pyridazinone (IV), which is treated first with Lawesson's reagent in hot dioxane and then with MeI and TEA in DMF to yield the methylsulfanyl pyridazine (V). The cyclization of (V) with acetamide (VI) by means of t-BuOLi in methanol/DMF affords the oxazolidinone (VII), which is finally treated with Lawesson's reagent in hot dioxane to provide the target thioacetamide.
| 【1】 Luehr, G.W.; Wang, S.; Hackbarth, C.J.; Gomez, M.; Trias, J.; Patel, D.V.; Gordeev, M.F.; Novel antimicrobial pyridazine phenyloxazolidinones. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-1320. |
| 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) | 61912 | benzyl 4-acetylphenylcarbamate | C16H15NO3 | 详情 | 详情 | |
| (II) | 15618 | 2-Oxoacetic acid; Glyoxylic Acid | 298-12-4 | C2H2O3 | 详情 | 详情 |
| (III) | 27344 | hydrazine | 302-01-2 | H4N2 | 详情 | 详情 |
| (IV) | 61913 | benzyl 4-(6-oxo-1,6-dihydro-3-pyridazinyl)phenylcarbamate | C18H15N3O3 | 详情 | 详情 | |
| (V) | 61914 | benzyl 4-[6-(methylsulfanyl)-3-pyridazinyl]phenylcarbamate | C19H17N3O2S | 详情 | 详情 | |
| (VI) | 61915 | (1S)-2-(acetylamino)-1-(chloromethyl)ethyl acetate | C7H12ClNO3 | 详情 | 详情 | |
| (VII) | 61916 | N-[((5S)-3-{4-[6-(methylsulfanyl)-3-pyridazinyl]phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide | C17H18N4O3S | 详情 | 详情 |