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【结 构 式】 
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【分子编号】54006 【品名】N-{(1R)-2-(ethylamino)-1-[(methylamino)methyl]ethyl}-4-methylbenzenesulfonamide 【CA登记号】n/a |
【 分 子 式 】C13H23N3O2S 【 分 子 量 】285.41064 【元素组成】C 54.71% H 8.12% N 14.72% O 11.21% S 11.24% |
合成路线1
该中间体在本合成路线中的序号：(VII)The protection of the NH2 group of L-serine (I) with Ts-Cl and TEA gives N-tosyl-L-serine (II), which is converted into the N-methylamide (III). The cyclization of (III) by means of diisopropylazodicarboxylate (DIAD) yields the N-tosylaziridine (IV), which is treated with ethylamine (V) to afford the diaminopropionamide (VI). The reduction of the amide group of (VI) with LiAlH4 provides the triaminopropane (VII), which is submitted to a reductive cyclization with glyoxal and BH3/TEA to give the perhydro-1,4-diazepine (VIII). Ts deprotection in (VIII) by means of HBr affords the 1-ethyl-4-methylperhydro-1,4-diazepin-6(R)-amine (IX), which is condensed with 5-bromo-2-methoxy-6-(methylamino)pyridine-3-carboxylic acid (X) by means of ethyl chloroformate and TEA to yield the target amide (XI). Finally, this compound is treated with fumaric acid (XII) in ethanol to afford the desired fumarate salt.
| 【1】 Hirokawa, Y.; et al.; Process development of the synthetic route to (R)-6-amino-1-ethyl-4-methylhexahydro-1,4-diazepine. Org Process Res Dev 2002, 6, 1, 28. |
| 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) | 20915 | methyl (2S)-2-amino-3-hydroxypropanoate | 5680-80-8 | C4H9NO3 | 详情 | 详情 |
| (II) | 54002 | methyl (2S)-3-hydroxy-2-{[(4-methylphenyl)sulfonyl]amino}propanoate | n/a | C11H15NO5S | 详情 | 详情 |
| (III) | 54003 | (2S)-3-hydroxy-N-methyl-2-{[(4-methylphenyl)sulfonyl]amino}propanamide | n/a | C11H16N2O4S | 详情 | 详情 |
| (IV) | 54004 | (2S)-N-methyl-1-[(4-methylphenyl)sulfonyl]-2-aziridinecarboxamide | n/a | C11H14N2O3S | 详情 | 详情 |
| (V) | 10928 | Ethanamine | 75-04-7 | C2H7N | 详情 | 详情 |
| (VI) | 54005 | (2S)-3-(ethylamino)-N-methyl-2-{[(4-methylphenyl)sulfonyl]amino}propanamide | n/a | C13H21N3O3S | 详情 | 详情 |
| (VII) | 54006 | N-{(1R)-2-(ethylamino)-1-[(methylamino)methyl]ethyl}-4-methylbenzenesulfonamide | n/a | C13H23N3O2S | 详情 | 详情 |
| (VIII) | 54007 | N-[(6S)-1-ethyl-4-methyl-1,4-diazepan-6-yl]-4-methylbenzenesulfonamide | n/a | C15H25N3O2S | 详情 | 详情 |
| (IX) | 17802 | (6S)-1-ethyl-4-methyl-1,4-diazepan-6-ylamine; (6S)-1-ethyl-4-methyl-1,4-diazepan-6-amine | C8H19N3 | 详情 | 详情 | |
| (X) | 17801 | 5-bromo-2-methoxy-6-(methylamino)nicotinic acid | C8H9BrN2O3 | 详情 | 详情 | |
| (XI) | 53998 | 5-bromo-N-[(6S)-1-ethyl-4-methyl-1,4-diazepan-6-yl]-2-methoxy-6-(methylamino)nicotinamide | n/a | C16H26BrN5O2 | 详情 | 详情 |
| (XII) | 23808 | Fumaric acid; (E)-2-butenedioic acid | 110-17-8 | C4H4O4 | 详情 | 详情 |