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【结 构 式】 
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【分子编号】12358 【品名】4-(Acetamido)-N-[(4-acetyl-1,4-oxazinan-2-yl)methyl]-2-ethoxybenzamide 【CA登记号】 |
【 分 子 式 】C18H25N3O5 【 分 子 量 】363.41372 【元素组成】C 59.49% H 6.93% N 11.56% O 22.01% |
合成路线1
该中间体在本合成路线中的序号：(III)The synthesis of the metabolites of mosapride, 4-amino-5-chloro-2-ethoxy-N-(2-morpholinylmethyl)benzamide (M-1) and 4-amino-5-chloro-2-ethoxy-N-(5-oxo-2-morpholinylmethyl)benzamide (M-2), has been described: 1) The hydrogenolysis of mosapride (I) with H2 over 10% Pd/C in aqueous ethanol/acetic acid gives 4-amino-2-ethoxy-N-(2-morpholinylmethyl)benzamide (II), which is acetylated with acetic anhydride in methanol/CHCl3, yielding the corresponding diacetyl derivative (III). The chlorination of (III) with N-chlorosuccinimide (NCS) in DMF affords the 5-chloro derivative (IV), which is finally deacetylated with refluxing 10% HCl, yielding the metabolite M-1 as the hydrochloride salt.
| 【1】 Kato, S.; Yoshida, N.; Morie, T.; Synthesis and biological activities of metabolites of mosapride, a new gastroprokinetic agent. Chem Pharm Bull 1995, 43, 4, 699. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (M-1) | 63425 | 2-methyl-1,2-dihydropyridine | C14H20ClN3O3 | 详情 | 详情 | |
| (I) | 12356 | 4-Amino-5-chloro-2-ethoxy-N-[[4-(4-fluorobenzyl)-1,4-oxazinan-2-yl]methyl]benzamide | C21H25ClFN3O3 | 详情 | 详情 | |
| (II) | 12357 | 4-Amino-2-ethoxy-N-(1,4-oxazinan-2-ylmethyl)benzamide | C14H21N3O3 | 详情 | 详情 | |
| (III) | 12358 | 4-(Acetamido)-N-[(4-acetyl-1,4-oxazinan-2-yl)methyl]-2-ethoxybenzamide | C18H25N3O5 | 详情 | 详情 | |
| (IV) | 12359 | 4-(Acetamido)-N-[(4-acetyl-1,4-oxazinan-2-yl)methyl]-5-chloro-2-ethoxybenzamide | C18H24ClN3O5 | 详情 | 详情 |