4-(2-methyl-1H-imidazol-1-yl)-2,2-diphenylbutanenitrile -Drug Synthesis Database

【结构式】

【分子编号】26218

【品名】4-(2-methyl-1H-imidazol-1-yl)-2,2-diphenylbutanenitrile

【CA登记号】

【分子式】C₂₀H₁₉N₃

【分子量】301.39108

【元素组成】C 79.7% H 6.35% N 13.94%

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：(IV)

Alkylation of diphenylacetonitrile (I) with dibromoethane provided bromide (II). This was condensed with 2-methylimidazole (III) in the presence of Et3N in DMF to afford the substituted imidazole (IV). Finally, hydrolysis of the cyano group of (IV) with 70% sulfuric acid produced the target amide.

参考文献中间体

合成目标

【1】 Miyachi, H.; et al.; Synthesis and antimuscarinic activity of a series of 4-(1-imidazolyl)-2,2-diphenylbutyramides: Discovery of potent and subtype-selective antimuscarinic agents. Bioorg Med Chem 1999, 7, 6, 1151.
【2】 Miyachi, H.; Okazaki, K.; Kiyota, H.; Segawa, M. (Kyorin Pharmaceutical Co., Ltd.); Novel imidazole deriv. and process for producing the same. EP 0733621; US 5932607; US 6103747; WO 9515951 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	10252	1,2-Dibromoethane; Ethylene dibromide	106-93-4	C₂H₄Br₂	详情	详情
(I)	14493	alpha-phenylbenzeneacetonitrile; 2,2-diphenylacetonitrile; Diphenylacetonitrile	86-29-3	C₁₄H₁₁N	详情	详情
(II)	26217	4-Bromo-2,2-diphenylbutyronitrile; 4-Bromo-2,2-diphenylbutanenitrile	39186-58-8	C₁₆H₁₄BrN	详情	详情
(III)	15670	2-Methylimidazole; 2-Methyl-1H-imidazole	693-98-1	C₄H₆N₂	详情	详情
(IV)	26218	4-(2-methyl-1H-imidazol-1-yl)-2,2-diphenylbutanenitrile		C₂₀H₁₉N₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

Treatment of acetonitrile derivative (I) with dibromoethane (II) in toluene in the presence of NaNH2 affords bromo compound (III), which is then condensed with imidazole derivative (IV) by means of Et3N in DMF to provide compound (V). Hydrolysis of the cyano group of (V) with aqueous H2SO4 yields amide derivative (VI), which is finally subjected to alkyl quaternization by reaction with bromobenzyl bromide (VI) in acetone to furnish the desired product.

参考文献中间体

合成目标

【1】 Miyachi, H.; Kiyota, H.; Segawa, M.; Design, synthesis and antimuscarinic activity of some imidazolium derivatives. Bioorg Med Chem Lett 1999, 9, 20, 3003.
【2】 Miyachi, H.; Okazaki, K.; Kiyota, H.; Segawa, M. (Kyorin Pharmaceutical Co., Ltd.); Novel imidazole deriv. and process for producing the same. EP 0733621; US 5932607; US 6103747; WO 9515951 .

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)	14493	alpha-phenylbenzeneacetonitrile; 2,2-diphenylacetonitrile; Diphenylacetonitrile	86-29-3	C₁₄H₁₁N	详情	详情
(II)	10252	1,2-Dibromoethane; Ethylene dibromide	106-93-4	C₂H₄Br₂	详情	详情
(III)	26217	4-Bromo-2,2-diphenylbutyronitrile; 4-Bromo-2,2-diphenylbutanenitrile	39186-58-8	C₁₆H₁₄BrN	详情	详情
(IV)	15670	2-Methylimidazole; 2-Methyl-1H-imidazole	693-98-1	C₄H₆N₂	详情	详情
(V)	26218	4-(2-methyl-1H-imidazol-1-yl)-2,2-diphenylbutanenitrile		C₂₀H₁₉N₃	详情	详情
(VI)	47152	4-(2-methyl-1H-imidazol-1-yl)-2,2-diphenylbutanamide	170105-16-5	C₂₀H₂₁N₃O	详情	详情
(VII)	16109	1-bromo-4-(bromomethyl)benzene; 4-Bromobenzyl bromide	589-15-1	C₇H₆Br₂	详情	详情

Extended Information