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【结 构 式】

【分子编号】47292

【品名】4-[(acetoxy)methyl]-3-(4-cyanobenzyl)-1-trityl-1H-imidazol-3-ium bromide

【CA登记号】

【 分 子 式 】C33H28BrN3O2

【 分 子 量 】578.50834

【元素组成】C 68.51% H 4.88% Br 13.81% N 7.26% O 5.53%

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:(XVI)

Protection of 4-(hydroxymethyl)imidazole (XII) with chlorotriphenylmethane provided the 1-tritylimidazole (XIII). Acetylation of (XIII) with acetic anhydride in pyridine gave acetate ester (XIV). The imidazole ring of (XIV) was then alkylated with alpha-bromo-p-tolunitrile (XV) to yield the imidazolium salt (XVI), from which the N-trityl group was removed upon heating with MeOH. The resulting acetoxymethyl imidazole (XVII) was then hydrolyzed to alcohol (XVIII) using LiOH, and further Swern oxidation of (XVIII) furnished aldehyde (XIX). Finally, reductive condensation of aldehyde (XIX) with piperazinone (VIII) in the presence of sodium triacetoxyborohydride produced the title compound.

1 Anthony, N.J.; Ciccarone, T.M.; Gomez, R.P.; Hutchinson, J.H.; Williams, T.M.; Dinsmore, C.J.; Stokker, G.E. (Merck & Co., Inc.); Inhibitors of farnesyl-protein transferase. EP 0820445; JP 1998511098; US 5856326; WO 9630343 .
2 Williams, T.M.; Dinsmore, C.J.; Hutchinson, J.H. (Merck & Co., Inc.); Inhibitors of prenyl-protein transferase. EP 1014984; WO 9909985 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VIII) 47289 1-(3-chlorophenyl)-2-piperazinone C10H11ClN2O 详情 详情
(XII) 42116 1H-imidazol-5-ylmethanol C4H6N2O 详情 详情
(XIII) 38392 (1-trityl-1H-imidazol-4-yl)methanol C23H20N2O 详情 详情
(XIV) 38391 (1-trityl-1H-imidazol-4-yl)methyl acetate C25H22N2O2 详情 详情
(XV) 14200 4-(Bromomethyl)benzonitrile; alpha-Bromo-p-tolunitrile 17201-43-3 C8H6BrN 详情 详情
(XVI) 47292 4-[(acetoxy)methyl]-3-(4-cyanobenzyl)-1-trityl-1H-imidazol-3-ium bromide C33H28BrN3O2 详情 详情
(XVII) 38390 [1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl acetate C14H13N3O2 详情 详情
(XVIII) 38389 4-[[5-(hydroxymethyl)-1H-imidazol-1-yl]methyl]benzonitrile C12H11N3O 详情 详情
(XIX) 38388 4-[(5-formyl-1H-imidazol-1-yl)methyl]benzonitrile C12H9N3O 详情 详情
Extended Information