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【结 构 式】 
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【药物名称】AU-130 【化学名称】4-(4-Amino-5-chloro-2-methoxybenzamido)piperidine-1-acetic acid 【CA登记号】145727-25-9 (mono HCl salt) 【 分 子 式 】C15H20ClN3O4 【 分 子 量 】341.79735 |
【开发单位】Abbott (Originator) 【药理作用】Gastric Emptying Disorders,Treatment of of, GASTROINTESTINAL DRUGS, Prokinetic Agents, 5-HT4 Agonists |
合成路线1
The condensation of 4-amino-5-chloro-2-methoxybenzoic acid (I) with 4-amino-1-(triphenylmethyl)piperidine (II) by means of ethyl chloroformate and triethylamine in THF gives the corresponding amide (III), which is deprotected with HCl in actone yielding 4-amino-5-chloro-2-methoxy-N-(4-piperidyl)benzamide (IV). The condensation of (IV) with ethyl bromoacetate (V) by means of K2CO3 in DMF affords the substituted acetate (VI), which is finally saponified with NaOH in methanol.
| 【1】 Ito, Y.; Kato, H.; Yasuda, S.; Iwasaki, N.; Nishino, H.; Takeshita, M. (Hokuriku Seiyaku Co., Ltd.); Benzamide deriv.. EP 0640601; US 5395832; US 5500422; WO 9214705 . |
| 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) | 12419 | 4-Amino-5-chloro-2-methoxybenzoic acid | 7206-70-4 | C8H8ClNO3 | 详情 | 详情 |
| (II) | 19955 | 1-trityl-4-piperidinylamine; 1-trityl-4-piperidinamine | C24H26N2 | 详情 | 详情 | |
| (III) | 19956 | 4-amino-5-chloro-2-methoxy-N-(1-trityl-4-piperidinyl)benzamide | C32H32ClN3O2 | 详情 | 详情 | |
| (IV) | 19957 | 4-amino-5-chloro-2-methoxy-N-(4-piperidinyl)benzamide | C13H18ClN3O2 | 详情 | 详情 | |
| (V) | 16640 | Ethyl 2-bromoacetate; Ethyl bromoacetate | 105-36-2 | C4H7BrO2 | 详情 | 详情 |
| (VI) | 19959 | ethyl 2-[4-[(4-amino-5-chloro-2-methoxybenzoyl)amino]-1-piperidinyl]acetate | C17H24ClN3O4 | 详情 | 详情 |