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【结 构 式】 
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【分子编号】47287 【品名】tert-butyl 2-[3-chloro(2-chloroacetyl)anilino]ethylcarbamate 【CA登记号】 |
【 分 子 式 】C15H20Cl2N2O3 【 分 子 量 】347.24088 【元素组成】C 51.88% H 5.81% Cl 20.42% N 8.07% O 13.82% |
合成路线1
该中间体在本合成路线中的序号：(VI)The synthesis of the intermediate (chlorophenyl)piperazinone (VIII) has been reported by two procedures. The hydrochloride salt prepared from 3-chloroaniline (I) was treated with 2-oxazolidinone (II) at 160 C to produce the aryl ethylenediamine (III), which was subsequently protected as the N-Boc derivative (IV). Acylation of aniline (IV) with chloroacetyl chloride (V) gave the chloroacetamide (VI). This was then cyclized to the piperazinone (VII) by treatment with K2CO3 in hot DMF. Further acid deprotection of the Boc group of (VII) afforded the intermediate (VIII).
| 【1】 Anthony, N.J.; Ciccarone, T.M.; Gomez, R.P.; Hutchinson, J.H.; Williams, T.M.; Dinsmore, C.J.; Stokker, G.E. (Merck & Co., Inc.); Inhibitors of farnesyl-protein transferase. EP 0820445; JP 1998511098; US 5856326; WO 9630343 . |
| 【2】 Williams, T.M.; Dinsmore, C.J.; Hutchinson, J.H. (Merck & Co., Inc.); Inhibitors of prenyl-protein transferase. EP 1014984; WO 9909985 . |
| 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) | 25239 | 3-chloroaniline; 3-chlorophenylamine | 108-42-9 | C6H6ClN | 详情 | 详情 |
| (II) | 21456 | 1,3-oxazolidin-2-one | 497-25-6 | C3H5NO2 | 详情 | 详情 |
| (III) | 37091 | C7H5Cl2FNO2P | 详情 | 详情 | ||
| (IV) | 47286 | tert-butyl 2-(3-chloroanilino)ethylcarbamate | C13H19ClN2O2 | 详情 | 详情 | |
| (V) | 11296 | 2-Chloroacetyl chloride; Chloroacetic chloride | 79-04-9 | C2H2Cl2O | 详情 | 详情 |
| (VI) | 47287 | tert-butyl 2-[3-chloro(2-chloroacetyl)anilino]ethylcarbamate | C15H20Cl2N2O3 | 详情 | 详情 | |
| (VII) | 47288 | tert-butyl 4-(3-chlorophenyl)-3-oxo-1-piperazinecarboxylate | C15H19ClN2O3 | 详情 | 详情 | |
| (VIII) | 47289 | 1-(3-chlorophenyl)-2-piperazinone | C10H11ClN2O | 详情 | 详情 |