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【结 构 式】

【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%

与该中间体有关的原料药合成路线共 1 条

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
Extended Information