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【结 构 式】 
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【分子编号】38298 【品名】3-[((3S)-3-[[(5-chlorothieno[3,2-b]pyridin-2-yl)sulfonyl]amino]-2-oxopyrrolidinyl)methyl]-4-hydroxybenzenecarboximidamide 【CA登记号】 |
【 分 子 式 】C19H18ClN5O4S2 【 分 子 量 】479.96792 【元素组成】C 47.55% H 3.78% Cl 7.39% N 14.59% O 13.33% S 13.36% |
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：(XIV)The reaction of 5-chlorothieno[3,2-b]pyridine (XI) with n-BuLi and SO2 in THF and further oxidation with SO2Cl2 gives sulfonyl chloride (XII), which was coupled with aminopyrrolidinone (X) by means of TEA in dichloromethane to yield sulfonamide (XIII). Conversion of the nitrile of (XIII) to the corresponding imidate with HCl in methanol, followed by reaction with ammonia produced benzamidine (XIV). Finally, hydrogenolytic dechlorination of (XIV) over Pd/C provided the title compound.
| 【1】 Ewing, W.R.; Davis, R.S.; Becker, M.R.; et al.; Synthesis, SAR and in vivo activity of novel thienopyridine sulfonamide pyrrolidinones as factor Xa inhibitors. Bioorg Med Chem Lett 1999, 9, 18, 2753. |
| 【2】 Ewing, W.R.; Becker, M.R.; Choi-Sledeski, Y.M.; Pauls, H.W.; McGarry, D.G.; Davis, R.S.; Spada, A.P. (Aventis Pharma SA); Substd. sulfonic acid N-[(aminoiminomethyl)phenylalkyl]-azaheterocyclamide cpds.. EP 0894088; JP 2000505815; US 5731315; WO 9824784 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (X) | 31677 | 3-[[(3S)-3-amino-2-oxopyrrolidinyl]methyl]-4-hydroxybenzonitrile | C12H13N3O2 | 详情 | 详情 | |
| (XI) | 38295 | 5-chlorothieno[3,2-b]pyridine | C7H4ClNS | 详情 | 详情 | |
| (XII) | 38296 | 5-chlorothieno[3,2-b]pyridine-2-sulfonyl chloride | C7H3Cl2NO2S2 | 详情 | 详情 | |
| (XIII) | 38297 | 5-chloro-N-[(3S)-1-(5-cyano-2-hydroxybenzyl)-2-oxopyrrolidinyl]thieno[3,2-b]pyridine-2-sulfonamide | C19H15ClN4O4S2 | 详情 | 详情 | |
| (XIV) | 38298 | 3-[((3S)-3-[[(5-chlorothieno[3,2-b]pyridin-2-yl)sulfonyl]amino]-2-oxopyrrolidinyl)methyl]-4-hydroxybenzenecarboximidamide | C19H18ClN5O4S2 | 详情 | 详情 |
Extended Information