|
【结 构 式】 
|
【分子编号】51328 【品名】4-amino-5-chloro-2-methoxybenzonitrile 【CA登记号】 |
【 分 子 式 】C8H7ClN2O 【 分 子 量 】182.60916 【元素组成】C 52.62% H 3.86% Cl 19.41% N 15.34% O 8.76% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(III)Benzamide (II) was prepared by treatment of the benzotriazolyl ester (I) with ammonium hydroxide in DMF. Dehydration of amide (II) with phosphorus oxychloride gave rise to nitrile (III), and subsequent addition of hydroxylamine to the cyano group of (III) furnished the N-hydroxybenzamidine (IV). Cyclization of (IV) with methyl 2-piperidineacetate (V) in the presence of NaH produced the oxadiazole compound (VI). Racemic (VI) was resolved employing L-ditoluoyltartaric acid, and the desired (S)-enantiomer was finally converted to the corresponding hydrochloride salt.
| 【1】 Suzuki, T.; Iwaoka, K.; Imanishi, N.; Nagakura, Y.; Miyata, K.; Nakahara, H.; Ohta, M.; Mase, T.; Synthesis of the selective 5-hydroxytryptamine 4 (5-HT4) receptor agonist (+)-(S)-2-chloro-5-methoxy-4-[5-(2-piperidylmethyl)-1,2,4-oxadiazol-3-yl]aniline. Chem Pharm Bull 1999, 47, 1, 120. |
| 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) | 18543 | 4-[(1H-1,2,3-benzotriazol-1-yloxy)carbonyl]-2-chloro-5-methoxyphenylamine; 4-[(1H-1,2,3-benzotriazol-1-yloxy)carbonyl]-2-chloro-5-methoxyaniline | C14H11ClN4O3 | 详情 | 详情 | |
| (II) | 51327 | 4-amino-5-chloro-2-methoxybenzamide | C8H9ClN2O2 | 详情 | 详情 | |
| (III) | 51328 | 4-amino-5-chloro-2-methoxybenzonitrile | C8H7ClN2O | 详情 | 详情 | |
| (IV) | 51329 | 4-amino-5-chloro-N'-hydroxy-2-methoxybenzenecarboximidamide | C8H10ClN3O2 | 详情 | 详情 | |
| (V) | 40753 | methyl 2-(2-piperidinyl)acetate | C8H15NO2 | 详情 | 详情 | |
| (VI) | 51330 | 2-chloro-5-methoxy-4-[5-(2-piperidinylmethyl)-1,2,4-oxadiazol-3-yl]aniline; 2-chloro-5-methoxy-4-[5-(2-piperidinylmethyl)-1,2,4-oxadiazol-3-yl]phenylamine | C15H19ClN4O2 | 详情 | 详情 |
Extended Information