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【结 构 式】 
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【分子编号】31344 【品名】1-[2-(4-benzyl-1-piperidinyl)-2-oxoethyl]-1H-indole-5-carbonitrile 【CA登记号】 |
【 分 子 式 】C23H23N3O 【 分 子 量 】357.45524 【元素组成】C 77.28% H 6.49% N 11.76% O 4.48% |
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：(VI)The alkylation of 5-cyanoindole (I) with methyl bromoacetate (II) in the presence of NaH in DMF provided the indolylacetate ester (III), which was hydrolyzed to the corresponding carboxylic acid (IV) with methanolic KOH. Coupling of (IV) with 4-benzylpiperidine (V) employing 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide-HCl (EDC) afforded amide (VI). Pinner reaction of (VI) with methanolic HCl produced imidate (VII), which was finally treated with ammonium carbonate in MeOH to yield the target amidine
| 【1】 Duffy, D.E.; Dominguez, C.; Han, Q.; et al.; Design and synthesis of potent and selective 5,6-fused heterocyclic thrombin inhibitors. Bioorg Med Chem Lett 1999, 9, 7, 925. |
| 【2】 Dominguez, C.; Han, Q.; Duffy, D.E.; Park, J.M.; Quan, M.L.; Rossi, K.A.; Wexler, R.R. (DuPont Pharmaceuticals Co.); Amidinoindoles, amidinoazoles, and analogs thereof as inhibitors of factor Xa and of thrombin. EP 0960102; WO 9801428 . |
| 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) | 31341 | 5-Cyanoindole; Indole-5-carbonitrile; 1H-Indole-5-carbonitrile | 15861-24-2 | C9H6N2 | 详情 | 详情 |
| (II) | 12309 | methyl 2-bromoacetate; methyl bromoacetate | 96-32-2 | C3H5BrO2 | 详情 | 详情 |
| (III) | 31342 | methyl 2-(5-cyano-1H-indol-1-yl)acetate | C12H10N2O2 | 详情 | 详情 | |
| (IV) | 31343 | 2-(5-cyano-1H-indol-1-yl)acetic acid | C11H8N2O2 | 详情 | 详情 | |
| (V) | 26225 | 4-benzylpiperidine | 31252-42-3 | C12H17N | 详情 | 详情 |
| (VI) | 31344 | 1-[2-(4-benzyl-1-piperidinyl)-2-oxoethyl]-1H-indole-5-carbonitrile | C23H23N3O | 详情 | 详情 | |
| (VII) | 31345 | methyl 1-[2-(4-benzyl-1-piperidinyl)-2-oxoethyl]-1H-indole-5-carboximidoate | C24H27N3O2 | 详情 | 详情 |
Extended Information