2,4-dimethyl-1H-imidazole -Drug Synthesis Database

【结构式】

【分子编号】20613

【品名】2,4-dimethyl-1H-imidazole

【CA登记号】930-62-1

【分子式】C₅H₈N₂

【分子量】96.132

【元素组成】C 62.47% H 8.39% N 29.14%

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：(II)

The condensation of 4-fluoro-2-methylnitrobenzene (I) with 2,4-dimethyl-1H-imidazole (II) by means of Na2CO3 in hot DMF gives 4-(2,4-dimethyl-1H-imidazol-1-yl)-2-methylnitrobenzene (III), which is reduced with SnCl2 in refluxing ethanol yielding the corresponding aniline (IV).The condensation of (IV) with trans-3-ethoxypropenoyl chloride in anhydrous pyridine affords the anilide (VI), which is finally cyclized by means of 98% H2SO4.

参考文献中间体

合成目标

【1】 Roberts, D.A.; Campbell, S.F. (Pfizer Inc.); Quinolone inotropic agents. AU 8543032; EP 0166533; ES 8608874; ES 8801797; JP 1986000082; US 4728653 .
【2】 Alabaster, C.T.; Bell, A.S.; Campbell, S.F.; Ellis, P.; Henderson, C.G.; Morris, D.S.; Roberts, D.A.; Ruddock, K.S.; Samuels, G.M.R.; Stefaniak, M.H.; 2(1H)-Quinolinones with cardiac stimulant activity. 2. Synthesis and biological activities of 6-(N-linked, five-membered heteroaryl) derivatives. J Med Chem 1989, 32, 3, 575-83.
【3】 Prous, J.; Castaner, J.; NANTERINONE < Prop INN>. Drugs Fut 1989, 14, 4, 328.

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)	20612	4-Fluoro-2-methyl-1-nitrobenzene; 2-Nitro-5-fluorotoluene	446-33-3	C₇H₆FNO₂	详情	详情
(II)	20613	2,4-dimethyl-1H-imidazole	930-62-1	C₅H₈N₂	详情	详情
(III)	20614	2,4-dimethyl-1-(3-methyl-4-nitrophenyl)-1H-imidazole		C₁₂H₁₃N₃O₂	详情	详情
(IV)	20615	4-(2,4-dimethyl-1H-imidazol-1-yl)-2-methylaniline; 4-(2,4-dimethyl-1H-imidazol-1-yl)-2-methylphenylamine		C₁₂H₁₅N₃	详情	详情
(V)	20616	(E)-3-ethoxy-2-propenoyl chloride	99471-66-6	C₅H₇ClO₂	详情	详情
(VI)	20617	(E)-N-[4-(2,4-dimethyl-1H-imidazol-1-yl)-2-methylphenyl]-3-ethoxy-2-propenamide		C₁₇H₂₁N₃O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

Acylation of 2,4-dimethylimidazole (I) with 2,4-dichlorobenzoyl chloride (II) in the presence of diisopropylethylamine, followed by acidic hydrolysis, provides the 2-imidazolyl acetophenone (III). Subsequent condensation of (III) with dimethylformamide dimethylacetal gives rise to the enaminone (IV)

参考文献中间体

合成目标

【1】 Brown, S.P.; Goff, D.; Ring, D.B.; Harrison, S.D.; Subramanian, S.; Nuss, J.M.; Boyce, R.S.; Johnson, K.; Pfister, K.B.; Ramurthy, S.; Renhowe, P.A.; Seely, L.; Wagman, A.S.; Zhou, X.A. (Chiron Corp.); Inhibitors of glycogen synthase kinase 3. EP 1087963; US 6417185; WO 9965897 .
【2】 Ring, D.B.; Harrison, S.D.; Nuss, J.M.; Boyce, R.S.; Johnson, K.; Pfister, K.B.; Ramurthy, S.; Seely, L.; Wagman, A.S.; Desai, M.; Levine, B.H. (Chiron Corp.); Inhibitors of glycogen synthase kinase 3. WO 0220495 .

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)	20613	2,4-dimethyl-1H-imidazole	930-62-1	C₅H₈N₂	详情	详情
(II)	35131	2,4-dichlorobenzoyl chloride; 2,4-Dichlorophenacylchloride	89-75-8	C₇H₃Cl₃O	详情	详情
(III)	60241	1-(2,4-dichlorophenyl)-2-(4-methyl-1H-imidazol-2-yl)-1-ethanone		C₁₂H₁₀Cl₂N₂O	详情	详情
(IV)	60242	1-(2,4-dichlorophenyl)-3-(dimethylamino)-2-(4-methyl-1H-imidazol-2-yl)-2-propen-1-one		C₁₅H₁₅Cl₂N₃O	详情	详情

Extended Information