methyl 4-[(2-butyl-4-chloro-5-formyl-1H-imidazol-1-yl)methyl]benzoate -Drug Synthesis Database

【结构式】

【分子编号】14573

【品名】methyl 4-[(2-butyl-4-chloro-5-formyl-1H-imidazol-1-yl)methyl]benzoate

【CA登记号】

【分子式】C₁₇H₁₉ClN₂O₃

【分子量】334.80224

【元素组成】C 60.99% H 5.72% Cl 10.59% N 8.37% O 14.34%

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：(XVI)

2) The condensation of 2-butyl-4-chloroimidazole-5-carbaldehyde (XV) with methyl 4-(bromomethyl)benzoate (VIII) by means of K2CO3 in DMF yields 4-(2-butyl-4-chloro-5-formylimidazol-1-ylmethyl)benzoic acid methyl ester (XVI), which is dechlorinated by hydrogenation with H2 over Pd/C in methanol affording compound (X). The condensation of (X) with 2-(2-thienylmethyl)malonic acid monomethyl ester (XVII) by means of piperidine/pyridine in toluene gives the previously described compound (XIV), which is finally saponified with KOH in ethanol.

参考文献中间体

合成目标

【1】 Wittenberger, S.J.; Tasker, A.; Sorensen, B.K.; Donner, B.G.; 2-Butyl-4-iodoimidazole-5-carboxaldehyde: A versatile intermediate for the synthesis of highly functionalized imidazoles. Synth Commun 1993, 23, 22, 3231-48.
【2】 Merlos, M.; Casas, A.; Graul, A.; Castaner, J.; Eprosartan. Drugs Fut 1997, 22, 10, 1079.
【3】 Keenan, R.M.; Weinstock, J.; Finkelstein, J.A.; et al.; Potent nonpeptide angiotensin II receptor antagonists. 2. 1-(Carboxybenzyl)imidazole-5-acrylic acids. J Med Chem 1993, 36, 13, 1880-92.
【4】 Weinstock, J.; Keenan, R.M.; Samanen, J.; et al.; 1-(Carboxybenzyl)imidazole-5-acrylic acids: Potent and selective angiotensin II receptor antagonists. J Med Chem 1991, 34, 4, 1514-7.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VIII)	14565	methyl 4-(bromomethyl)benzoate	2417-72-3	C₉H₉BrO₂	详情	详情
(X)	14567	methyl 4-[(2-butyl-5-formyl-1H-imidazol-1-yl)methyl]benzoate		C₁₇H₂₀N₂O₃	详情	详情
(XIV)	14571	methyl 4-([2-butyl-5-[(E)-3-methoxy-3-oxo-2-(2-thienylmethyl)-1-propenyl]-1H-imidazol-1-yl]methyl)benzoate		C₂₅H₂₈N₂O₄S	详情	详情
(XV)	13925	2-Butyl-4-chloro-1H-imidazole-5-carbaldehyde	83857-96-9	C₈H₁₁ClN₂O	详情	详情
(XVI)	14573	methyl 4-[(2-butyl-4-chloro-5-formyl-1H-imidazol-1-yl)methyl]benzoate		C₁₇H₁₉ClN₂O₃	详情	详情
(XVII)	14574	3-methoxy-3-oxo-2-(2-thienylmethyl)propionic acid		C₉H₁₀O₄S	详情	详情

Extended Information