TAK-661
3-(7-异丙醇[1,2,4]三唑并[1,5-b]吡啶嗪-6-酰氧基)-2,2-二甲基丙烷磺胺Chemical Name: 3-(7-Isopropyl[1,2,4]triazolo[1,5-b]pyridazin-6-yloxy)-2,2-dimethylpropanesulfonamide
CAS No. 175215-34-6
项目整合开发状态: Phase II
项目研究机构: Takeda (Originator)
合成路线:Treatment of 3,6-dichloro-4-isopropylpyridazine (I) with ethanolic ammonia in a sealed tube at 130-140 C provided aminopyridazine (II).Subsequent condensation of (II) with dimethylformamide dimethyl acetal in boiling toluene,followed by reaction with hydroxylamine hydrochloride furnished the formamide oxime (III).This was cyclized to the triazolopyridazine (IV) using polyphosphoric acid at 110 C.The remaining chloro atom of (IV) was finally displaced by 3-hydroxy-2,2-dimethyl-1-propanesulfonamide (V) in the presence of NaH in refluxing THF.
📌 参考资料/链接：
参考文献标题:Triazolopyridazines as antiasthmatics
文献作者:Miyake,A.; Kawano,Y.; Ashida,A.(Takeda Chemical Industries,Ltd.)
参考来源:EP 0562439; JP 1994279447; US 5389633; US 5482939
📄 详细内容
合成路线:Treatment of 3,6-dichloro-4-isopropylpyridazine (I) with ethanolic ammonia in a sealed tube at 130-140 C provided aminopyridazine (II).Subsequent condensation of (II) with dimethylformamide dimethyl acetal in boiling toluene,followed by reaction with hydroxylamine hydrochloride furnished the formamide oxime (III).This was cyclized to the triazolopyridazine (IV) using polyphosphoric acid at 110 C.The remaining chloro atom of (IV) was finally displaced by 3-hydroxy-2,2-dimethyl-1-propanesulfonamide (V) in the presence of NaH in refluxing THF.
参考文献标题:Triazolopyridazines process and intermediates for their preparation and their use as medicaments
文献作者:Kawano,Y.; Miyake,A.; Ashida,Y.(Takeda Chemical Industries,Ltd.)
参考来源:EP 0781283; JP 1996198878; JP 1997328485; WO 9608496
产品链接: CAS No. 175215-34-6››