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【结 构 式】 
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【分子编号】12332 【品名】methyl 4-(acetamido)-5-chloro-2-ethoxybenzoate 【CA登记号】 |
【 分 子 式 】C12H14ClNO4 【 分 子 量 】271.7002 【元素组成】C 53.05% H 5.19% Cl 13.05% N 5.16% O 23.55% |
合成路线1
该中间体在本合成路线中的序号：(III)The starting compounds (IV) and (VII) are obtained as follows: a) Methyl 4-acetylamino-2-hydroxybenzoate (I) is converted to the 2-ethoxy derivative (II) with ethyl iodide, and then chlorination of (II) with N-chlorosuccinimide followed by alkaline hydrolysis of (III) gives benzoic acid (IV). b) The reaction of 2-[(4-fluorobenzyl)amino]ethanol (V) with N-(2,3-epoxypropyl)phthalimide (VI), followed by treatment with concentrated sulfuric acid, affords intermediate (VII). The condensation of 4-Amino-5-chloro-2-ethoxybenzoic acid (IV) with 4-(4-fluorobenzyl)-2-(methylamino) morpholine (VII) by means of ethyl chloroformate and triethylamine in CHCl3 gives 4-amino-5-chloro-2-ethoxy-N-[[4-(4-fluorobenzyl)-2-morpholinyl]methyl] benzamide, which is converted to mosapride citrate, by treatment with citric acid.
| 【1】 Kato, S.; Yoshida, N.; Ito, T.; Mosapride Citrate. Drugs Fut 1993, 18, 6, 513. |
| 【2】 Kato, S.; Morie, T.; Hino, K.; Kon, T.; Naruto, S.; Yoshida, N.; Karasawa, T.; Matsumoto, J.; Novel benzamides as selective and potent gastrokinetic agents. 1. Synthesis and structure-activity relationships of N[4-(2-morpholinyl)alkyl]benzamides. J Med Chem 1990, 33, 5, 1406-13. |
| 【3】 Kato, S.; Morie, T.; Hino, K.; Kon, T.; Naruto, S.; Yoshida, N.; Karasawa, T.; Matsumoto, J.; Novel benzamides as selective and potent gastrokinetic agents. 1. Synthesis and structure-activity relationships of N[4-(2-morpholinyl)alkyl]benzamides. J Med Chem 1990, 33, 5, 1406-13. |
| 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) | 12330 | methyl 4-(acetamido)-2-hydroxybenzoate | C10H11NO4 | 详情 | 详情 | |
| (II) | 12331 | Methyl 4-acetamido-2-ethoxybenzoate; methyl 4-(acetamido)-2-ethoxybenzoate | 59-06-3 | C12H15NO4 | 详情 | 详情 |
| (III) | 12332 | methyl 4-(acetamido)-5-chloro-2-ethoxybenzoate | C12H14ClNO4 | 详情 | 详情 | |
| (IV) | 12333 | 4-Amino-5-chloro-2-ethoxybenzoic acid | C9H10ClNO3 | 详情 | 详情 | |
| (V) | 12334 | 2-[(4-Fluorobenzyl)amino]-1-ethanol | C9H12FNO | 详情 | 详情 | |
| (VI) | 12335 | 2-(2-Oxiranylmethyl)-1H-isoindole-1,3(2H)-dione; N-(2,3-Epoxypropyl)phtalimide | 5455-98-1 | C11H9NO3 | 详情 | 详情 |
| (VII) | 12336 | [4-(4-Fluorobenzyl)-1,4-oxazinan-2-yl]methylamine; [4-(4-Fluorobenzyl)-1,4-oxazinan-2-yl]methanamine; 2-Aminomethyl-4-(4-fluorobenzyl)morpholine | 112914-13-3 | C12H17FN2O | 详情 | 详情 |