2-(2-ethoxyphenyl)-5-methyl-7-propylimidazo[5,1-f][1,2,4]triazin-4(3H)-one -Drug Synthesis Database

【结构式】

【分子编号】44354

【品名】2-(2-ethoxyphenyl)-5-methyl-7-propylimidazo[5,1-f][1,2,4]triazin-4(3H)-one

【CA登记号】

【分子式】C₁₇H₂₀N₄O₂

【分子量】312.37156

【元素组成】C 65.37% H 6.45% N 17.94% O 10.24%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(IV)

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.

参考文献中间体

合成目标

【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：(IV)

参考文献中间体

合成目标

【1】 Heim-Riether A, Healy J. 2005. A novel method for the synthesis of imidazo[5,1-f][1,2,4 ]triazin-4(3H) -ones. J Org Chem, 70 (18): 7331～7337

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	66941	4-methyl-2-propyl-1H-imidazole-5-carboxamide	C₈H₁₃N₃O	详情	详情
(II)	66942	1-amino-4-methyl-2-propyl-1H-imidazole-5-carboxamide	C₈H₁₄N₅O	详情	详情
(III)	66943	1-(2-ethoxybenzamido)-4-methyl-2-propyl-1H-imidazole-5-carboxamide	C₁₇H₂₂N₅O₃	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

Extended Information