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【结 构 式】

【分子编号】35842

【品名】2-[(benzyloxy)methyl]-5-iodo-4-isopropyl-1H-imidazole; benzyl (5-iodo-4-isopropyl-1H-imidazol-2-yl)methyl ether

【CA登记号】

【 分 子 式 】C14H17IN2O

【 分 子 量 】356.20633

【元素组成】C 47.21% H 4.81% I 35.63% N 7.86% O 4.49%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VII)

Cyclization of 2,2-dichloroisobutyraldehyde (I) - obtained by reaction of isovaleraldehyde (II) with chlorine in DMF - with 2-benzyloxyacetaldehyde (III) - produced by reaction of 2-butene-1,4-diol (IV) with benzyl chloride by means of NaOH in water, followed by ozonolysis in MeOH and finally reduction with triphenylphosphine in ethyl acetate - and aqueous NH4OH in methanol gives the imidazole derivative (VI), which is iodinated with I2 and NaOH in dichloromethane to yield the 5-iodoimidaz-ole derivative (VII). Condensation of compound (VII) with bis(3,5-dichlorophenyl)disulfide (VIII) by means of LiH in DMSO affords the dichlorophenylsulfanyl imidazole (IX), which is alkylated with 4-(chloromethyl)pyridine (X) and K2CO3 in DMF to provide the fully substituted imidazole (XI). Debenzylation of compound (XI) with conc. HCl in refluxing ethanol gives the carbinol (XII), which is finally treated with trichloroacetyl isocyanate and triethylamine in methanol/water.

1 Sorbera, L.A.; Castañer, J.; Bayes, M.; Capravirine. Drugs Fut 2003, 28, 12, 1149.
2 Sugita, K.; Makino, I.; Sugimoto, H.; et al.; Synthesis and biological activity of imidazole derivatives as a novel class of HIV-1 nonnucleoside reverse transcriptase inhibitors. Symp Med Chem 1999, Abst 2P-05.
3 Aono, K.; Ichihashi, T.; Sugawara, T.; Hirano, K. (Shionogi & Co. Ltd.); Lymph-absorbable imidazole derivs.. EP 0893442; US 6054591; WO 9735843 .
4 Sugimoto, H.; Fujiwara, T. (Shionogi & Co. Ltd.); Imidazole deriv.. EP 0786455; US 5910506; US 6147097; WO 9610019 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
40725 2,2,2-trichloroacetyl isocyanate 3019-71-4 C3Cl3NO2 详情 详情
(I) 35840 2,2-dichloro-3-methylbutanal C5H8Cl2O 详情 详情
(II) 26052 3-methylbutanal 590-86-3 C5H10O 详情 详情
(III) 17346 Benzyloxyacetaldehyde; 2-(Benzyloxy)acetaldehyde 60656-87-3 C9H10O2 详情 详情
(IV) 36995 4-[2-(1-piperidinyl)ethoxy]benzoyl chloride C14H18ClNO2 详情 详情
(V) 63296 1-({[(Z)-4-(benzyloxy)-2-butenyl]oxy}methyl)benzene; benzyl (Z)-4-(benzyloxy)-2-butenyl ether C18H20O2 详情 详情
(VI) 35841 benzyl (4-isopropyl-1H-imidazol-2-yl)methyl ether; 2-[(benzyloxy)methyl]-4-isopropyl-1H-imidazole C14H18N2O 详情 详情
(VII) 35842 2-[(benzyloxy)methyl]-5-iodo-4-isopropyl-1H-imidazole; benzyl (5-iodo-4-isopropyl-1H-imidazol-2-yl)methyl ether C14H17IN2O 详情 详情
(VIII) 35843 bis(3,5-dichlorophenyl) disulfide; 1,3-dichloro-5-[(3,5-dichlorophenyl)disulfanyl]benzene 137897-99-5 C12H6Cl4S2 详情 详情
(IX) 35844 benzyl [5-[(3,5-dichlorophenyl)sulfanyl]-4-isopropyl-1H-imidazol-2-yl]methyl ether; 2-[(benzyloxy)methyl]-5-[(3,5-dichlorophenyl)sulfanyl]-4-isopropyl-1H-imidazole C20H20Cl2N2OS 详情 详情
(X) 10844 4-(Chloromethyl)pyridine 10445-91-7 C6H6ClN 详情 详情
(XI) 35845 4-([2-[(benzyloxy)methyl]-5-[(3,5-dichlorophenyl)sulfanyl]-4-isopropyl-1H-imidazol-1-yl]methyl)pyridine; benzyl [5-[(3,5-dichlorophenyl)sulfanyl]-4-isopropyl-1-(4-pyridinylmethyl)-1H-imidazol-2-yl]methyl ether C26H25Cl2N3OS 详情 详情
(XII) 35846 [5-[(3,5-dichlorophenyl)sulfanyl]-4-isopropyl-1-(4-pyridinylmethyl)-1H-imidazol-2-yl]methanol C19H19Cl2N3OS 详情 详情
Extended Information