(E)-4-(4-methoxy-3,5-dimethyl-2-pyridinyl)-3-buten-2-one -Drug Synthesis Database

【结构式】

【分子编号】18788

【品名】(E)-4-(4-methoxy-3,5-dimethyl-2-pyridinyl)-3-buten-2-one

【CA登记号】

【分子式】C₁₂H₁₅NO₂

【分子量】205.25664

【元素组成】C 70.22% H 7.37% N 6.82% O 15.59%

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：(V)

Reaction of chloromethylpyridine (I) with NaOH in aqueous THF afforded alcohol (II), which was oxidized to formylpyridine (III) with selenium dioxide in refluxing pyridine. Subsequent condensation of aldehyde (III) with phosphorane (IV) in THF provided enone (V), and this was hydrogenated in the presence of Pd/C in MeOH to give (VI). Finally, condensation of ketone (VI) with aminothiophenol (VII) in the presence of p-toluenesulfonic acid in refluxing benzene yielded the corresponding benzothiazolidine.

参考文献中间体

合成目标

【1】 Yoon, S.-H.; Seo, S.; Lee, Y.; Hwang, S.; Kim, D.Y.; Syntheses of 2-[(3,5-dimethyl-4-methoxypyridyl)alkyl]benzothiazolidine derivatives as a potential gstric H+/K+-ATPase inhibitor. Bioorg Med Chem Lett 1998, 8, 14, 1909.

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)	16521	2-(chloromethyl)-3,5-dimethyl-4-pyridinyl methyl ether; 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine; 2-Chloromethyl-3,5-dimethyl-4-methoxypyridine	86604-75-3	C₉H₁₂ClNO	详情	详情
(II)	18785	(4-methoxy-3,5-dimethyl-2-pyridinyl)methanol		C₉H₁₃NO₂	详情	详情
(III)	18786	4-methoxy-3,5-dimethyl-2-pyridinecarbaldehyde		C₉H₁₁NO₂	详情	详情
(IV)	18787	1-(triphenylphosphoranylidene)acetone	1439-36-7	C₂₁H₁₉OP	详情	详情
(V)	18788	(E)-4-(4-methoxy-3,5-dimethyl-2-pyridinyl)-3-buten-2-one		C₁₂H₁₅NO₂	详情	详情
(VI)	18789	4-(4-methoxy-3,5-dimethyl-2-pyridinyl)-2-butanone		C₁₂H₁₇NO₂	详情	详情
(VII)	12097	2-Amino-4-(trifluoromethyl)benzenethiol; 2-Amino-4-(trifluoromethyl)phenylhydrosulfide		C₇H₆F₃NS	详情	详情

Extended Information