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【结 构 式】 
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【分子编号】50470 【品名】ethyl 3-cyano-2-oxopropanoate 【CA登记号】 |
【 分 子 式 】C6H7NO3 【 分 子 量 】141.12652 【元素组成】C 51.06% H 5% N 9.92% O 34.01% |
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：(I)The condensation of ethyl cyanopyruvate (I) with 2-fluorobenzyl hydrazine (II) in the presence of trifluoroacetic acid produced the aminopyrazole (III). This was further condensed with (dimethylamino)acrolein (IV) under acidic conditions to furnish the pyrazolopyridine (V). The ethyl ester group of (V) was then converted to nitrile (VII) via formation of the corresponding amide (VI), followed by dehydration with trifluoroacetic anhydride. Addition of methoxide to the cyano group of (VII) produced imidate (VIII), which was treated with ammonium chloride to yield the amidine (IX).
| 【1】 Starub, A.; et al.; NO-independent stimulators of soluble guanylate cyclase. Bioorg Med Chem Lett 2001, 11, 6, 781. |
| 【2】 Feurer, A.; Stahl, E.; Stasch, J.-P.; Straub, A.; Dembowsky, K.; Alonso-Alija, C.; Perzborn, E.; Hutter, J. (Bayer AG); Substd. pyrazole derivs.. DE 19834047; EP 1102767; WO 0006568 . |
| 【3】 Straub, A.; Alonso-Alija, C.; Preiss, M.; Janichen, J. (Bayer AG); Method for the production of substd. pyrimidine derivs.. DE 19942809; WO 0117998 . |
| 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) | 50470 | ethyl 3-cyano-2-oxopropanoate | C6H7NO3 | 详情 | 详情 | |
| (II) | 50471 | 1-(2-fluorobenzyl)hydrazine | 51859-98-4 | C7H9FN2 | 详情 | 详情 |
| (III) | 50472 | ethyl 5-amino-1-(2-fluorobenzyl)-1H-pyrazole-3-carboxylate | 256504-39-9 | C13H14FN3O2 | 详情 | 详情 |
| (IV) | 11789 | (E)-3-(Dimethylamino)-2-propenal | 692-32-0 | C5H9NO | 详情 | 详情 |
| (V) | 50473 | ethyl 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxylate | 256376-59-7 | C16H14FN3O2 | 详情 | 详情 |
| (VI) | 50474 | 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxamide | 256376-62-2 | C14H11FN4O | 详情 | 详情 |
| (VII) | 50475 | 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile | 256376-65-5 | C14H9FN4 | 详情 | 详情 |
| (VIII) | 50476 | methyl 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidoate | 304874-06-4 | C15H13FN4O | 详情 | 详情 |
| (IX) | 50477 | 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide | 256376-68-8 | C14H12FN5 | 详情 | 详情 |
Extended Information