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【结 构 式】 
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【分子编号】18582 【品名】4-(3-pyridinyl)-5-isoxazolamine; 4-(3-pyridinyl)-5-isoxazolylamine 【CA登记号】 |
【 分 子 式 】C8H7N3O 【 分 子 量 】161.1632 【元素组成】C 59.62% H 4.38% N 26.07% O 9.93% |
合成路线1
该中间体在本合成路线中的序号：(IV)Condensation of 3-pyridylacetonitrile (I) with dimethyl-formamide dimethylacetal (II) afforded dimethylaminomethylene compound (III), which was cyclized to isoxazole (IV) by treatment with hydroxylamine.HCl in AcOH at 100 C. Quaternization with iodomethane provided pyridinium salt (V), and subsequent reduction with NaBH4 in MeOH produced tetrahydropyridine (VI). Then, methylation with iodomethane in the presence of KOH gave a mixture of monomethylated (VII) and dimethylated (VIII) compounds, which were separated by column chromatography. Finally, the major methylamino compound (VII) was converted to the oxalate salt.
| 【1】 Olesen, P.H.; Swedberg, M.D.B.; Rimvall, K.; 3-(5-Alkylamino-4-isoxazolyl)-1,2,5,6-tetrahydropyridines: A novel class of central nicotinic receptor ligands. Bioorg Med Chem 1998, 6, 9, 1623. |
| 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) | 18579 | 2-(3-pyridinyl)acetonitrile | 6443-85-2 | C7H6N2 | 详情 | 详情 |
| (II) | 11984 | N-(Dimethoxymethyl)-N,N-dimethylamine;dimethylformamide dimethylacetal;1,1-dimethoxy-N,N-dimethylmethanamine； Dimethoxy-N,N-dimethylmethanamine; N,N-Dimethylformamide dimethyl acetal | 4637-24-5 | C5H13NO2 | 详情 | 详情 |
| (III) | 18581 | (Z)-3-(dimethylamino)-2-(3-pyridinyl)-2-propenenitrile | C10H11N3 | 详情 | 详情 | |
| (IV) | 18582 | 4-(3-pyridinyl)-5-isoxazolamine; 4-(3-pyridinyl)-5-isoxazolylamine | C8H7N3O | 详情 | 详情 | |
| (V) | 18583 | 3-(5-amino-4-isoxazolyl)-1-methylpyridinium iodide | C9H10IN3O | 详情 | 详情 | |
| (VI) | 18584 | 4-(1-methyl-1,2,5,6-tetrahydro-3-pyridinyl)-5-isoxazolamine; 4-(1-methyl-1,2,5,6-tetrahydro-3-pyridinyl)-5-isoxazolylamine | C9H13N3O | 详情 | 详情 | |
| (VII) | 18585 | N-methyl-N-[4-(1-methyl-1,2,5,6-tetrahydro-3-pyridinyl)-5-isoxazolyl]amine; N-methyl-4-(1-methyl-1,2,5,6-tetrahydro-3-pyridinyl)-5-isoxazolamine | C10H15N3O | 详情 | 详情 | |
| (VIII) | 18586 | N,N-dimethyl-N-[4-(1-methyl-1,2,5,6-tetrahydro-3-pyridinyl)-5-isoxazolyl]amine; N,N-dimethyl-4-(1-methyl-1,2,5,6-tetrahydro-3-pyridinyl)-5-isoxazolamine | C11H17N3O | 详情 | 详情 |