NSC-624548, HO-221
N-[[4-(5-溴嘧啶-2-基)氧基-3-氯苯基]氨基甲酰]-2-(羟基-氧代氨基)苯甲酰胺Chemical Name: N-(2-Nitrobenzoyl)-N'-[4-(5-bromo-2-pyrimidinyloxy)-3-chlorophenyl]urea; N-[4-(5-Bromo-2-pyrimidinyloxy)-3-chlorophenyl]-N'-(2-nitrobenzoyl)urea
CAS No. 105128-93-6
项目整合开发状态: Phase I
项目研究机构: Mitsubishi Pharma (Originator)
合成路线:1) The condensation of 4-amino-2-chlorophenol (I) with 5 bromo-2-chloropyrimidine (II) by means of K2CO3 in hot DMSO gives 4-(5-bromo-2-pyrimidinyloxy)-3-chloroaniline (III),which is then condensed with 2-nitrobenzoyl isocyanate (IV) in dioxane.
合成路线:2) The reaction of aniline (III) with phosgene in ethyl acetate gives 4-(5-bromo-2-pyrimidinyloxy)-3-chlorophenyl isocyanate (V),which is then condensed with 2-nitrobenzamide (VI) in refluxing toluene.
合成路线:3) The reaction of aminophenol (I) with isocyanate (IV) in dioxane gives N-(2-nitrobenzoyl(-N'-(3-chloro-4-hydroxyphenyl)urea (VII),which is then condensed with pyrimidine (II) by means of KOH in hot DMSO.
📌 参考资料/链接：
参考文献标题:Benzoyl urea cpds.,process for their production,
文献作者:Haga,T.; Kondo,N.; Koyanagi,T.; Nakajima,T.; Sugi,H.; Watanabe,M.; Yamada,N.; Yokoyama,K.(Ishihara Sangyo Kaisha,Ltd.)
参考来源:CH 671576; EP 0192235; FR 2577551; GB 2171695; US 4727077
📄 详细内容
合成路线:1) The condensation of 4-amino-2-chlorophenol (I) with 5 bromo-2-chloropyrimidine (II) by means of K2CO3 in hot DMSO gives 4-(5-bromo-2-pyrimidinyloxy)-3-chloroaniline (III),which is then condensed with 2-nitrobenzoyl isocyanate (IV) in dioxane.
合成路线:2) The reaction of aniline (III) with phosgene in ethyl acetate gives 4-(5-bromo-2-pyrimidinyloxy)-3-chlorophenyl isocyanate (V),which is then condensed with 2-nitrobenzamide (VI) in refluxing toluene.
合成路线:3) The reaction of aminophenol (I) with isocyanate (IV) in dioxane gives N-(2-nitrobenzoyl(-N'-(3-chloro-4-hydroxyphenyl)urea (VII),which is then condensed with pyrimidine (II) by means of KOH in hot DMSO.
参考文献标题:HO-221
文献作者:Hoshi,A.; Prous,J.; Castar,J.
参考来源:Drugs Fut 1988,13(9),822
产品链接: CAS No. 105128-93-6››