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【结 构 式】 
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【分子编号】46962 【品名】ethyl 1-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-6,8-dimethoxy-4-isoquinolinecarboxylate 【CA登记号】 |
【 分 子 式 】C23H20N2O6 【 分 子 量 】420.42168 【元素组成】C 65.71% H 4.79% N 6.66% O 22.83% |
合成路线1
该中间体在本合成路线中的序号：(V)Acylation of ethyl 3-amino-2-(3,5-dimethoxyphenyl)propionate (I) with N-phthaloylglycine (II) using EDC and HOAt afforded amide (III), which was subjected to a Bischler-Napieralski cyclization in the presence of POCl3 to produce the dihydroisoquinoline (IV). Aromatization of (IV) to the corresponding isoquinoline (V) was achieved by treatment with MnO2 in refluxing benzene. Hydrazinolysis of the phthaloyl group of (V) gave the free amine, which was purified after conversion to the N-Boc derivative (VI). Acid cleavage of the Boc group then furnished the title product.
| 【1】 Coppola, G.M.; et al.; 1-Aminomethylisoquinoline-4-carboxylates as novel dipeptidylpeptidase IV inhibitors. Bioorg Med Chem Lett 2000, 10, 14, 1555. |
| 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) | 46959 | ethyl 3-amino-2-(3,5-dimethoxyphenyl)propanoate | C13H19NO4 | 详情 | 详情 | |
| (II) | 10284 | N-Phthaloylglycine; 2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)acetic acid | 4702-13-0 | C10H7NO4 | 详情 | 详情 |
| (III) | 46960 | ethyl 2-(3,5-dimethoxyphenyl)-3-[[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetyl]amino]propanoate | C23H24N2O7 | 详情 | 详情 | |
| (IV) | 46961 | ethyl 1-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-6,8-dimethoxy-3,4-dihydro-4-isoquinolinecarboxylate | C23H22N2O6 | 详情 | 详情 | |
| (V) | 46962 | ethyl 1-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-6,8-dimethoxy-4-isoquinolinecarboxylate | C23H20N2O6 | 详情 | 详情 | |
| (VI) | 46963 | ethyl 1-[[(tert-butoxycarbonyl)amino]methyl]-6,8-dimethoxy-4-isoquinolinecarboxylate | C20H26N2O6 | 详情 | 详情 |