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【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

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.

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 CAS号 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.

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 CAS号 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