|
【结 构 式】 
|
【分子编号】24396 【品名】methyl (2S)-2-isocyanato-3-(2,3,4,5,6-pentafluorophenyl)propanoate 【CA登记号】 |
【 分 子 式 】C11H6F5NO3 【 分 子 量 】295.165596 【元素组成】C 44.76% H 2.05% F 32.18% N 4.75% O 16.26% |
合成路线1
该中间体在本合成路线中的序号：(II)Pentafluorophenylalanine methyl ester (I) was treated with phosgene and pyridine to afford isocyanate (II), which was condensed with 5-aminothiadiazole-2-thione (III) to provide urea (IV). Then, displacement of the ester function of (IV) with 1-(2-pyridyl)piperazine (V) furnished the title amide.
| 【1】 Mitchell, M.A.; Hendges, S.K.; Jacobsen, E.J.; et al.; Synthesis of a series of stromelysin-selective thiadiazole urea matrix metalloproteinase inhibitors. J Med Chem 1999, 42, 9, 1525. |
| 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) | 24395 | methyl (2S)-2-amino-3-(2,3,4,5,6-pentafluorophenyl)propanoate | C10H8F5NO2 | 详情 | 详情 | |
| (II) | 24396 | methyl (2S)-2-isocyanato-3-(2,3,4,5,6-pentafluorophenyl)propanoate | C11H6F5NO3 | 详情 | 详情 | |
| (III) | 24397 | 5-amino-1,3,4-thiadiazole-2(3H)-thione | 2349-67-9 | C2H3N3S2 | 详情 | 详情 |
| (IV) | 24398 | methyl (2S)-3-(2,3,4,5,6-pentafluorophenyl)-2-([[(5-thioxo-4,5-dihydro-1,3,4-thiadiazol-2-yl)amino]carbonyl]amino)propanoate | C13H9F5N4O3S2 | 详情 | 详情 | |
| (V) | 24399 | 1-(2-pyridinyl)piperazine | 34803-66-2 | C9H13N3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(II)Pentafluorophenylalanine methyl ester (I) was treated with phosgene and pyridine to afford isocyanate (II), which was condensed with 5-aminothiadiazole-2-thione (III) to provide urea (IV). Then, displacement of the ester function of (IV) with methylamine furnished the title amide.
| 【1】 Mitchell, M.A.; Hendges, S.K.; Jacobsen, E.J.; et al.; Synthesis of a series of stromelysin-selective thiadiazole urea matrix metalloproteinase inhibitors. J Med Chem 1999, 42, 9, 1525. |
| 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) | 24395 | methyl (2S)-2-amino-3-(2,3,4,5,6-pentafluorophenyl)propanoate | C10H8F5NO2 | 详情 | 详情 | |
| (II) | 24396 | methyl (2S)-2-isocyanato-3-(2,3,4,5,6-pentafluorophenyl)propanoate | C11H6F5NO3 | 详情 | 详情 | |
| (III) | 24397 | 5-amino-1,3,4-thiadiazole-2(3H)-thione | 2349-67-9 | C2H3N3S2 | 详情 | 详情 |
| (IV) | 24398 | methyl (2S)-3-(2,3,4,5,6-pentafluorophenyl)-2-([[(5-thioxo-4,5-dihydro-1,3,4-thiadiazol-2-yl)amino]carbonyl]amino)propanoate | C13H9F5N4O3S2 | 详情 | 详情 |