[4-isopropyl-1-(4-pyridinylmethyl)-1H-imidazol-2-yl]methanol -Drug Synthesis Database

【结构式】

【分子编号】63301

【品名】[4-isopropyl-1-(4-pyridinylmethyl)-1H-imidazol-2-yl]methanol

【CA登记号】

【分子式】C₁₃H₁₇N₃O

【分子量】231.2976

【元素组成】C 67.51% H 7.41% N 18.17% O 6.92%

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：(XVIII)

Debenzylation of 2-(benzyloxymethyl)-4-isopropyl-1-(4-pyridylmethyl)-1H-imidazole (XVI) with hot aqueous HCl gives the hydroxymethyl derivative (XVIII), which is condensed with chlorosulfonyl isocyanate in ethyl acetate to yield carbamic acid 1-(4-pyridylmethyl)-4-isopropyl-1H-imidazol-2-ylmethyl ester (XIX). Finally, this compound is condensed with 3,5-dichlorophenylsulfanyl chloride (XVII) by means of triethylamine in DMF/toluene.

参考文献中间体

合成目标

【1】 Sorbera, L.A.; Castañer, J.; Bayes, M.; Capravirine. Drugs Fut 2003, 28, 12, 1149.
【2】 Kabaki, M.; Hajima, M.; Hozumi, Y. (Shionogi & Co. Ltd.); Process for producing imidazole derivs.. EP 0949249; US 6057448; WO 9829395 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XVI)	63299	benzyl [4-isopropyl-1-(4-pyridinylmethyl)-1H-imidazol-2-yl]methyl ether; 4-({2-[(benzyloxy)methyl]-4-isopropyl-1H-imidazol-1-yl}methyl)pyridine	C₂₀H₂₃N₃O	详情	详情
(XVII)	63000	methyl 6-[3-(1-adamantyl)-5-bromo-4-methoxyphenyl]-5-bromo-2-naphthoate; methyl 6-[3-(1-adamantyl)-5-bromo-4-methoxyphenyl]-5-bromo-2-naphthoate	C₂₉H₂₈Br₂O₃	详情	详情
(XVIII)	63301	[4-isopropyl-1-(4-pyridinylmethyl)-1H-imidazol-2-yl]methanol	C₁₃H₁₇N₃O	详情	详情
(XIX)	63302	[4-isopropyl-1-(4-pyridinylmethyl)-1H-imidazol-2-yl]methyl carbamate	C₁₄H₁₈N₄O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XVIII)

Esterification of 4-isopropyl-1-(4-pyridylmethyl)-1H-imidazol-2-ylmethanol (XVIII) by means of acetyl chloride and triethylamine in dichloromethane gives the acetate ester (XX), which is condensed with 3,5-dichlorophenylsulfanyl chloride (XVII) by means of triethylamine in toluene/acetonitrile to yield the thioether (XXI). Hydrolysis of the acetate group of compound (XXI) by means of NaOH in ethanol affords the hydroxymethyl compound (XII), which is finally condensed with chlorosulfonyl isocyanate in acetonitrile.

参考文献中间体

合成目标

【1】 Sorbera, L.A.; Castañer, J.; Bayes, M.; Capravirine. Drugs Fut 2003, 28, 12, 1149.
【2】 Kabaki, M.; Hajima, M.; Hozumi, Y. (Shionogi & Co. Ltd.); Process for producing imidazole derivs.. EP 0949249; US 6057448; WO 9829395 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XII)	35846	[5-[(3,5-dichlorophenyl)sulfanyl]-4-isopropyl-1-(4-pyridinylmethyl)-1H-imidazol-2-yl]methanol	C₁₉H₁₉Cl₂N₃OS	详情	详情
(XVII)	63300	3,5-dichlorobenzenesulfenyl chloride	C₆H₃Cl₃S	详情	详情
(XVIII)	63301	[4-isopropyl-1-(4-pyridinylmethyl)-1H-imidazol-2-yl]methanol	C₁₃H₁₇N₃O	详情	详情
(XX)	63303	[4-isopropyl-1-(4-pyridinylmethyl)-1H-imidazol-2-yl]methyl acetate	C₁₅H₁₉N₃O₂	详情	详情
(XXI)	63304	[5-[(3,5-dichlorophenyl)sulfanyl]-4-isopropyl-1-(4-pyridinylmethyl)-1H-imidazol-2-yl]methyl acetate	C₂₁H₂₁Cl₂N₃O₂S	详情	详情

Extended Information