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【结 构 式】 
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【分子编号】42248 【品名】N-(2-azidophenethyl)-N-methylamine; 2-(2-azidophenyl)-N-methyl-1-ethanamine 【CA登记号】 |
【 分 子 式 】C9H12N4 【 分 子 量 】176.22124 【元素组成】C 61.34% H 6.86% N 31.79% |
合成路线1
该中间体在本合成路线中的序号：(VIII)Acetonitrile derivative (I) is treated with BuLi and alkylated with 3-bromopropanol (A) to yield alcohol (II), which is further alkylated by means of LICKOR (n-BuLi/t-BuOK) and 1-chloro-3-bromopropane (B) to afford (III). Reaction of derivative (III) with secondary amine (VIII) in acetonitrile gives (IV). Amine (VIII) is obtained by trifluoroacetylation of azide (VI) with trifluoroacetic anhydride to yield (VII), which is then N-methylated by means of MeI and hydrolyzed with KOH. Finally, alcohol (IV) reacts with succinimido biotinate (V) in DMSO to provide the desired product.
| 【1】 Teodori, E.; et al.; Synthesis and binding properties of photoactivable biotin-conjugated verapamil derivatives for the study of P-170 glycoprotein. Bioorg Med Chem 1999, 7, 9, 1873. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 12573 | 3-Bromo-1-propanol; 3-Bromopropanol | 627-18-9 | C3H7BrO | 详情 | 详情 |
| (B) | 19490 | 3-chloro-1-propanol | 627-30-5 | C3H7ClO | 详情 | 详情 |
| (I) | 25857 | 2-(3,4-dimethoxyphenyl)acetonitrile | 93-17-4 | C10H11NO2 | 详情 | 详情 |
| (II) | 42244 | 2-(3,4-dimethoxyphenyl)-5-hydroxypentanenitrile | C13H17NO3 | 详情 | 详情 | |
| (III) | 42245 | 5-chloro-2-(3,4-dimethoxyphenyl)-2-(3-hydroxypropyl)pentanenitrile | C16H22ClNO3 | 详情 | 详情 | |
| (IV) | 42249 | 5-[(2-azidophenethyl)(methyl)amino]-2-(3,4-dimethoxyphenyl)-2-(3-hydroxypropyl)pentanenitrile | C25H33N5O3 | 详情 | 详情 | |
| (V) | 42250 | 1-([5-[(3aS,4S,6aR)-3a,4,6a-trimethyl-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoyl]oxy)-2,5-pyrrolidinedione | C17H25N3O5S | 详情 | 详情 | |
| (VI) | 42246 | 2-azidophenethylamine; 2-(2-azidophenyl)-1-ethanamine | C8H10N4 | 详情 | 详情 | |
| (VII) | 42247 | N-(2-azidophenethyl)-2,2,2-trifluoroacetamide | C10H9F3N4O | 详情 | 详情 | |
| (VIII) | 42248 | N-(2-azidophenethyl)-N-methylamine; 2-(2-azidophenyl)-N-methyl-1-ethanamine | C9H12N4 | 详情 | 详情 |