4-methyl-4H-1,2,4-triazole-3-thiol; 4-methyl-4H-1,2,4-triazol-3-ylhydrosulfide -Drug Synthesis Database

【结构式】

【分子编号】44993

【品名】4-methyl-4H-1,2,4-triazole-3-thiol; 4-methyl-4H-1,2,4-triazol-3-ylhydrosulfide

【CA登记号】

【分子式】C₃H₅N₃S

【分子量】115.15892

【元素组成】C 31.29% H 4.38% N 36.49% S 27.84%

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：(VII)

Bromoacetophenone (I) was converted into a cis/trans mixture of ketals (III) by treatment with glycerin (II) and p-toluenesulfonic acid. Subsequent reaction of (III) with 2-naphthalenesulfonyl chloride gave the corresponding mixture of sulfonate esters. After separation of the desired cis-isomer (IV), its condensation with the phenol derivative (V) produced ether (VI). Finally, displacement of the bromine atom of (VI) with 3-mercapto-4-methyl-1,2,4-triazole (VII) using Na2CO3 in DMF gave rise to the title thioether.

参考文献中间体

合成目标

【1】 Backx, L.; Meerpoel, L.; Heeres, J.; et al.; Structure-activity relationship of a novel chemical family of MTP inhibitors with lipid-lowering properties. 16th Int Symp Med Chem (Sept 18 2000, Bologna) 2000, Abst PA-142.

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)	16720	2-bromo-1-(4-chlorophenyl)-1-ethanone; 2-Bromo-4'-chloroacetophenone	536-38-9	C₈H₆BrClO	详情	详情
(II)	13289	Glycerine; Glycerin; Glycerol	56-81-5	C₃H₈O₃	详情	详情
(III)	44994	[2-(bromomethyl)-2-(4-chlorophenyl)-1,3-dioxolan-4-yl]methanol		C₁₁H₁₂BrClO₃	详情	详情
(IV)	44990	[(2S,4S)-2-(bromomethyl)-2-(4-chlorophenyl)-1,3-dioxolan-4-yl]methyl 2-naphthalenesulfonate		C₂₁H₁₈BrClO₅S	详情	详情
(V)	44991	4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-2-[(1R)-1-methylpropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one		C₂₂H₂₇N₅O₂	详情	详情
(VI)	44992	4-[4-[4-(4-[[(2S,4R)-2-(bromomethyl)-2-(4-chlorophenyl)-1,3-dioxolan-4-yl]methoxy]phenyl)-1-piperazinyl]phenyl]-2-[(1R)-1-methylpropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one		C₃₃H₃₇BrClN₅O₄	详情	详情
(VII)	44993	4-methyl-4H-1,2,4-triazole-3-thiol; 4-methyl-4H-1,2,4-triazol-3-ylhydrosulfide		C₃H₅N₃S	详情	详情

Extended Information