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【结 构 式】 
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【分子编号】16871 【品名】2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethylamine; 2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]-1-ethanamine 【CA登记号】 |
【 分 子 式 】C13H15N5 【 分 子 量 】241.2958 【元素组成】C 64.71% H 6.27% N 29.02% |
合成路线1
该中间体在本合成路线中的序号：(XI)2) The condensation of 4-nitrobenzyl bromide (VI) with 1,2,4-triazole sodium salt (VII) in DMF gives 1-(4-nitrobenzyl)-1,2,4-triazole (VIII), which is reduced with H2 over Pd/C in ethanol/ethyl acetate yielding the aniline (I). The diazotization of (I) with NaNO2/HCl followed by reduction with SnCl2 affords the corresponding hydrazine (IX), which is cyclized with 4-chlorobutanal dimethylacetal (X) by means of HCl in refluxing ethanol/water to afford 2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl] ethylamine (XI). Finally, this amine is methylated with formaldehyde, sodium cyanoborohydride and acetic acid in methanol.
| 【1】 Castañer, J.; Mealy, N.; Rabassseda, X.; MK-0462. Drugs Fut 1995, 20, 7, 676. |
| 【2】 Baker, R.; Matassa, V.G.; Street, L.J. (Merck Sharp & Dohme Ltd.); Imidazole, triazole and tetrazole derivs. EP 0497512; EP 0778275; US 5298520; US 5451588; US 5602162; US 5602163 . |
| 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) | 16860 | 4-(1H-1,2,4-triazol-1-ylmethyl)aniline; 4-(1H-1,2,4-triazol-1-ylmethyl)phenylamine | C9H10N4 | 详情 | 详情 | |
| (VI) | 16866 | 1-(Bromomethyl)-4-nitrobenzene; para-Nitrobenzyl bromide | 100-11-8 | C7H6BrNO2 | 详情 | 详情 |
| (VII) | 13104 | 1,2,4-Triazole, sodium derivative | 41253-21-8 | C2H2N3Na | 详情 | 详情 |
| (VIII) | 16868 | 1-(4-nitrobenzyl)-1H-1,2,4-triazole | C9H8N4O2 | 详情 | 详情 | |
| (IX) | 16869 | 1-(4-hydrazinobenzyl)-1H-1,2,4-triazole | C9H11N5 | 详情 | 详情 | |
| (X) | 16870 | 4-Chlorobutyraldehyde dimethylacetal; 4-Chloro-1-methoxybutyl methyl ether; 4-Chloro-1,1-dimethoxybutane | C6H13ClO2 | 详情 | 详情 | |
| (XI) | 16871 | 2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethylamine; 2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]-1-ethanamine | C13H15N5 | 详情 | 详情 |