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【结 构 式】 
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【分子编号】44992 【品名】4-[4-[4-(4-[[(2S,4R)-2-(bromomethyl)-2-(4-chlorophenyl)-1,3-dioxolan-4-yl]methoxy]phenyl)-1-piperazinyl]phenyl]-2-[(1R)-1-methylpropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one 【CA登记号】 |
【 分 子 式 】C33H37BrClN5O4 【 分 子 量 】683.04478 【元素组成】C 58.03% H 5.46% Br 11.7% Cl 5.19% N 10.25% O 9.37% |
合成路线1
该中间体在本合成路线中的序号：(VI)Bromoacetophenone (I) was converted into a cis/trans mixture of ketals (III) by treatment with glycerin (II) and p-toluenesulfonic acid. Subsequent reaction of (III) with 2-naphthalenesulfonyl chloride gave the corresponding mixture of sulfonate esters. After separation of the desired cis-isomer (IV), its condensation with the phenol derivative (V) produced ether (VI). Finally, displacement of the bromine atom of (VI) with 3-mercapto-4-methyl-1,2,4-triazole (VII) using Na2CO3 in DMF gave rise to the title thioether.
| 【1】 Backx, L.; Meerpoel, L.; Heeres, J.; et al.; Structure-activity relationship of a novel chemical family of MTP inhibitors with lipid-lowering properties. 16th Int Symp Med Chem (Sept 18 2000, Bologna) 2000, Abst PA-142. |
| 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) | 16720 | 2-bromo-1-(4-chlorophenyl)-1-ethanone; 2-Bromo-4'-chloroacetophenone | 536-38-9 | C8H6BrClO | 详情 | 详情 |
| (II) | 13289 | Glycerine; Glycerin; Glycerol | 56-81-5 | C3H8O3 | 详情 | 详情 |
| (III) | 44994 | [2-(bromomethyl)-2-(4-chlorophenyl)-1,3-dioxolan-4-yl]methanol | C11H12BrClO3 | 详情 | 详情 | |
| (IV) | 44990 | [(2S,4S)-2-(bromomethyl)-2-(4-chlorophenyl)-1,3-dioxolan-4-yl]methyl 2-naphthalenesulfonate | C21H18BrClO5S | 详情 | 详情 | |
| (V) | 44991 | 4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-2-[(1R)-1-methylpropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one | C22H27N5O2 | 详情 | 详情 | |
| (VI) | 44992 | 4-[4-[4-(4-[[(2S,4R)-2-(bromomethyl)-2-(4-chlorophenyl)-1,3-dioxolan-4-yl]methoxy]phenyl)-1-piperazinyl]phenyl]-2-[(1R)-1-methylpropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one | C33H37BrClN5O4 | 详情 | 详情 | |
| (VII) | 44993 | 4-methyl-4H-1,2,4-triazole-3-thiol; 4-methyl-4H-1,2,4-triazol-3-ylhydrosulfide | C3H5N3S | 详情 | 详情 |