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【结 构 式】 
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【分子编号】27509 【品名】2,6-dichloro-3-nitrobenzyl 5-isoquinolinyl ether 【CA登记号】 |
【 分 子 式 】C16H10Cl2N2O3 【 分 子 量 】349.17248 【元素组成】C 55.04% H 2.89% Cl 20.31% N 8.02% O 13.75% |
合成路线1
该中间体在本合成路线中的序号：(VI)Nitration of 2,6-dichlorobenzaldehyde (I) with 70% HNO3 in concentrated H2SO4 at ice-bath temperature provided the 3-nitro derivative (II). This was reduced with NaBH4 in MeOH at 10 C to the alcohol (III), which was treated with mesyl chloride and triethylamine in dichloromethane to give mesylate (IV). Alkylation of 5-hydroxyisoquinoline (V) with mesylate (IV) in the presence of NaH in DMF yielded ether (VI). Subsequent reduction of the nitro group of (VI) with hydrazine and FeCl3 provided amine (VII), which was finally acylated with Ac2O in dichloroethane at 70 C to furnish the target acetamide.
| 【1】 Satoh, S.; Kayakiri, H.; Abe, Y.; et al.; A novel class of orally active non-peptide bradykinin B2 receptor antagonists. 1. Construction of the basic framework. J Med Chem 1998, 41, 4, 564. |
| 【2】 Yoshida, Y.; Barrett, D.; Azami, H.; Morinaga, C.; Matsumoto, Y.; Takasugi, H.; Discovery of a novel benzyloxyisoquinoline derivative with potent anti-Helicobacter pylori activity. Bioorg Med Chem Lett 1998, 8, 14, 1897. |
| 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) | 27507 | 2,6-dichlorobenzaldehyde | 83-38-5 | C7H4Cl2O | 详情 | 详情 |
| (II) | 27508 | 2,6-dichloro-3-nitrobenzaldehyde | C7H3Cl2NO3 | 详情 | 详情 | |
| (III) | 18590 | (2,6-dichloro-3-nitrophenyl)methanol | C7H5Cl2NO3 | 详情 | 详情 | |
| (IV) | 19295 | 2,6-dichloro-3-nitrobenzyl methanesulfonate | C8H7Cl2NO5S | 详情 | 详情 | |
| (V) | 18668 | 5-isoquinolinol | 2439-04-5 | C9H7NO | 详情 | 详情 |
| (VI) | 27509 | 2,6-dichloro-3-nitrobenzyl 5-isoquinolinyl ether | C16H10Cl2N2O3 | 详情 | 详情 | |
| (VII) | 27510 | 2,4-dichloro-3-[(5-isoquinolinyloxy)methyl]aniline | C16H12Cl2N2O | 详情 | 详情 |