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【结 构 式】 
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【分子编号】44352 【品名】2-ethoxybenzenecarboximidamide 【CA登记号】53623-81-7 |
【 分 子 式 】C9H12N2O 【 分 子 量 】164.20716 【元素组成】C 65.83% H 7.37% N 17.06% O 9.74% |
与该中间体有关的原料药合成路线共 2 条
合成路线1
该中间体在本合成路线中的序号：(I)Cyclization of 2-ethoxybenzamidine (I) with 2-butyramidopropionic acid (II) and ethoxalyl chloride (III) by means of DMAP in refluxing pyridine gives 2-(2-ethoxyphenyl)-5-methyl-7-propyl-3,4-dihydroimidazo[5,1-f][1,2,4]triazin-4-one (IV), which is sulfonated with chlorosulfonic acid to provide the sulfonyl chloride (V). Finally, this compound is condensed with 1-ethylpiperazine (VI) in dichloromethane.
| 【1】 Niewohner, U.; Bischoff, E.; Es-Sayed, M.; Schenke, T.; Schmidt, G.; Lampe, T.; Haning, H.; Imidazo[5,1-f][1,2,4]triazin-4(3H)-ones, a new class of potent PDE 5 inhibitors. Bioorg Med Chem Lett 2002, 12, 6, 865. |
| 【2】 Castaner, J.; Martin, L.; Rabasseda, X.; Sorbera, L.A.; Vardenafil. Drugs Fut 2001, 26, 2, 141. |
| 【3】 Perzborn, E.; Keldenich, J.; Schlemmer, K.-H.; Haning, H.; Serno, P.; Bischoff, E.; El-Sayed, M.; Niewöhner, U.; Nowakowski, M.; Schenke, T.; Dembowsky, K. (Bayer AG); 2-Phenyl substd. imidazotriazinones as phosphodiesterase inhibitors. DE 19750085; DE 19812462; EP 1049695; WO 9924433 . |
| 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) | 44352 | 2-ethoxybenzenecarboximidamide | 53623-81-7 | C9H12N2O | 详情 | 详情 |
| (II) | 44353 | N-butyrylalanine | C7H13NO3 | 详情 | 详情 | |
| (III) | 11043 | Ethyl 2-chloro-2-oxoacetate; Ethyl oxalyl chloride | 4755-77-5 | C4H5ClO3 | 详情 | 详情 |
| (IV) | 44354 | 2-(2-ethoxyphenyl)-5-methyl-7-propylimidazo[5,1-f][1,2,4]triazin-4(3H)-one | C17H20N4O2 | 详情 | 详情 | |
| (V) | 44355 | 4-ethoxy-3-(5-methyl-4-oxo-7-propyl-3,4-dihydroimidazo[5,1-f][1,2,4]triazin-2-yl)benzenesulfonyl chloride | C17H19ClN4O4S | 详情 | 详情 | |
| (VI) | 14213 | N-Ethylpiperazine; 1-Ethylpiperazine | 5308-25-8 | C6H14N2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(V)
| 【1】 Chen L. Ma YH. Xie F. et al. 2006. The synthesis of a phosphodiesterase (V) inhibitor varderiafil. 化学世界，28 (5), 287～289 |
| 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) | 31032 | alanine | 302-72-7 | C3H7NO2 | 详情 | 详情 |
| (II) | 44353 | N-butyrylalanine | C7H13NO3 | 详情 | 详情 | |
| (III) | 66944 | ethyl 3-butyramido-2-oxobutanoate | C10H17NO4 | 详情 | 详情 | |
| (IV) | 66945 | 2-ethoxybenzonitrile | 6609-57-0 | C9H9NO | 详情 | 详情 |
| (V) | 44352 | 2-ethoxybenzenecarboximidamide | 53623-81-7 | C9H12N2O | 详情 | 详情 |
| (VI) | 66946 | N-(1-(3-(2-ethoxyphenyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)ethyl)butyramide | C17H22N4O3 | 详情 | 详情 | |
| (VII) | 66947 | 2-(2-ethoxyphenyl)-5-methyl-7-propylimidazo[1,5-b]pyridazin-4(1H)-one | C18H21N3O2 | 详情 | 详情 | |
| (VIII) | 66948 | 4-ethoxy-3-(5-methyl-4-oxo-7-propyl-1,4-dihydroimidazo[1,5-b]pyridazin-2-yl)benzenesulfonic acid | C18H21N3O5S | 详情 | 详情 | |
| (IX) | 66949 | 4-ethoxy-3-(5-methyl-4-oxo-7-propyl-1,4-dihydroimidazo[1,5-b]pyridazin-2-yl)benzene-1-sulfonyl chloride | C18H20ClN3O4S | 详情 | 详情 |
Extended Information