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【结 构 式】 
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【分子编号】63367 【品名】5-{[(5-nitro-1-benzofuran-2-yl)carbonyl]amino}-1H-indole-2-carboxylic acid 【CA登记号】 |
【 分 子 式 】C18H11N3O6 【 分 子 量 】365.30196 【元素组成】C 59.18% H 3.04% N 11.5% O 26.28% |
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：(IV)Coupling between ethyl 5-aminoindole-2-carboxylate (I) and 5-nitrobenzofuran-2-carboxylic acid (II) by means of HBTU affords amide (III). Subsequent ethyl ester hydrolysis under alkaline conditions yields the carboxylic acid (IV). Ring opening of the cyclopropane-fused compound (V) with anhydrous HCl in EtOAc leads to the chloromethyl compound (VI). Acid (IV) is finally coupled to amine (VI) in the presence of EDC to furnish the title compound.
| 【1】 Wang, Y.; Li, L.; Ye, W.; Tian, Z.; Jiang, W.; Wang, H.; Wright, S.C.; Larrick, J.W.; CC-1065 analogues bearing different DNA-binding subunits: Synthesis, antitumor activity, and preliminary toxicity study. J Med Chem 2003, 46, 4, 634. |
| 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) | 38164 | ethyl 5-amino-1H-indole-2-carboxylate | C11H12N2O2 | 详情 | 详情 | |
| (II) | 63365 | 5-nitro-1-benzofuran-2-carboxylic acid | 10242-12-3 | C9H5NO5 | 详情 | 详情 |
| (III) | 63366 | ethyl 5-{[(5-nitro-1-benzofuran-2-yl)carbonyl]amino}-1H-indole-2-carboxylate | C20H15N3O6 | 详情 | 详情 | |
| (IV) | 63367 | 5-{[(5-nitro-1-benzofuran-2-yl)carbonyl]amino}-1H-indole-2-carboxylic acid | C18H11N3O6 | 详情 | 详情 | |
| (V) | 40978 | 1,2,2a,3,9,9a-hexahydro-4H-benzo[e]cyclopropa[c]indol-4-one | C13H13NO | 详情 | 详情 | |
| (VI) | 40977 | 1-(chloromethyl)-2,3-dihydro-1H-benzo[e]indol-5-ol | C13H12ClNO | 详情 | 详情 |
Extended Information