methyl 1H-imidazole-4-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】27998

【品名】methyl 1H-imidazole-4-carboxylate

【CA登记号】17325-26-7

【分子式】C₅H₆N₂O₂

【分子量】126.11492

【元素组成】C 47.62% H 4.8% N 22.21% O 25.37%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(I)

The Grignard condensation of methyl imidazole-4-carboxyate (I) with 2,3-dimethylphenylmagnesium bromide (II) in THF gives 4-(2,3-dimethylbenzoyl) imidazole (III), which (without isolation) is submitted to a new Grignard condensation with methylmagnesium iodide (IV) in the same solvent to yield 1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethanol (V). The dehydration of (V) with potassium hydrogen sulfate at 136 C affords 1-(4-imidazolyl)-1-(2,3-dimethyl-phenyl)ethylene (VI), which is finally hydrogenated with H2 over Pd/C in 2N HCl.

参考文献中间体

合成目标

【1】 Hillier, K.; Acta Univ Oul 1981, 8, 4, A125.
【2】 Karjalainen, A.J.; Kurkela, K.O.A.; Pohjala, E.K. (Orion Pharma); Antihypertensive subtituted imidazole derivates. GB 2101114; US 4639464 .
【3】 Castaner, R.M.; Serradell, M.N.; Castaner, J.; Medetomidine. Drugs Fut 1987, 12, 11, 1021.

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)	27998	methyl 1H-imidazole-4-carboxylate	17325-26-7	C₅H₆N₂O₂	详情	详情
(II)	27999	bromo(2,3-dimethylphenyl)magnesium		C₈H₉BrMg	详情	详情
(III)	11040	(2,3-Dimethylphenyl)(1H-imidazol-4-yl)methanone		C₁₂H₁₂N₂O	详情	详情
(IV)	20225	iodo(methyl)magnesium	917-64-6	CH₃IMg	详情	详情
(V)	28000	1-(2,3-dimethylphenyl)-1-(1H-imidazol-4-yl)-1-ethanol		C₁₃H₁₆N₂O	详情	详情
(VI)	28001	4-[1-(2,3-dimethylphenyl)vinyl]-1H-imidazole		C₁₃H₁₄N₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

参考文献中间体

合成目标

【1】 Karjalainen AJ, Pohjala EK, et aL 1983. Substituted imidazole derivatives and their use. GB Pat 2101114
【2】 Karjalainen AJ, Virtanen RE, et aL 1989. Preparation and testing of medetomidine enantiomers as CNS agents GB Pat. 2206880

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)	27998	methyl 1H-imidazole-4-carboxylate	17325-26-7	C₅H₆N₂O₂	详情	详情
(II)	27999	bromo(2,3-dimethylphenyl)magnesium		C₈H₉BrMg	详情	详情
(III)	66258	1-(2,3-dimethylphenyl)-1-(1H-imidazol-4-yl)ethanol		C₁₃H₁₆N₂O	详情	详情
(IV)	66259	4-(1-(2,3-dimethylphenyl)ethyl)-1H-imidazole		C₁₃H₁₆N₂	详情	详情

Extended Information