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【结 构 式】 
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【分子编号】57158 【品名】2-ethyl-6,7-dihydro-1-benzofuran-4(5H)-one 【CA登记号】 |
【 分 子 式 】C10H12O2 【 分 子 量 】164.20408 【元素组成】C 73.15% H 7.37% O 19.49% |
合成路线1
该中间体在本合成路线中的序号：(I)The cyclization of 2-ethyl-4,5,6,7-tetrahydrobenzofuran-4-one (I) with ethyl formate and hydrazine by means of tBu-OK in THF gives the furo[2,3-g]indazole derivative (II), which is aromatized by means of DDQ in dioxane, yielding intermediate (III). Finally, this compound is condensed with N-(tert-butoxycarbonyl)-O-(tosyl)-L-alaninol (IV) by means of Cs2CO3 in DMF, followed by a treatment with HCl to afford the target YM-348. Alternatively, intermediate (III) is condensed with (R)-propylene oxide (V) by means of NaH in THF to give the propanol derivative (VI), which is treated first with mesyl chloride and TEA in dichloromethane, and then with Na-N3 in DMF to yield the azide (VII). Finally, this compound is reduced with LiAlH4 in THF to afford the target amine YM-348.
| 【1】 Shimada, I.; et al.; Synthesis and structure-activity relationship of a series of indazole derivatives as 5-HT2C receptor agonists. 22nd Symp Med Chem (Nov 27 2002, Shizuoka) 2002, Abst 2P-20. |
| 【2】 Maeno, K.; Kazuta, K.; Shimada, I.; et al.; Synthesis and structure-activity relationships of a series of substituted 2-(1H-furo[2,3-g]indazol-1-yl)ethylamine derivatives as 5-HT2C receptor agonists. 224th ACS Natl Meet (Aug 18 2002, Boston) 2002, Abst MEDI 348. |
| 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) | 57158 | 2-ethyl-6,7-dihydro-1-benzofuran-4(5H)-one | C10H12O2 | 详情 | 详情 | |
| (II) | 57159 | 7-ethyl-4,5-dihydro-1H-furo[2,3-g]indazole | C11H12N2O | 详情 | 详情 | |
| (III) | 57160 | 7-ethyl-1H-furo[2,3-g]indazole | C11H10N2O | 详情 | 详情 | |
| (IV) | 57161 | (2S)-2-[(tert-butoxycarbonyl)amino]propyl 4-methylbenzenesulfonate | C15H23NO5S | 详情 | 详情 | |
| (V) | 16662 | (2R)-2-Methyloxirane; (R)-(+)-Propylene oxide | 15448-47-2 | C3H6O | 详情 | 详情 |
| (VI) | 57162 | (2R)-1-(7-ethyl-1H-furo[2,3-g]indazol-1-yl)-2-propanol | C14H16N2O2 | 详情 | 详情 | |
| (VII) | 57163 | 1-[(2S)-2-azidopropyl]-7-ethyl-1H-furo[2,3-g]indazole; (1S)-2-(7-ethyl-1H-furo[2,3-g]indazol-1-yl)-1-methylethyl azide | C14H15N5O | 详情 | 详情 |