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【结 构 式】

【分子编号】48641

【品名】1-[[4'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-carbaldehyde

【CA登记号】

【 分 子 式 】C18H13F3N2O

【 分 子 量 】330.3093096

【元素组成】C 65.45% H 3.97% F 17.26% N 8.48% O 4.84%

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:(XIII)

The mercaptoimidazole (IX) was prepared by condensation between 4-bromobenzylamine (VII), 1,3-dihydroxyacetone (VIII) and potassium thiocyanate. Oxidative desulfuration of (IX) with hydrogen peroxide in acidic medium yielded imidazole (X). The biphenyl derivative (XII) was obtained by Suzuki coupling of aryl bromide (X) with 4-(trifluoromethyl)benzeneboronic acid (XI). Subsequent oxidation of the alcohol group of (XII) under Swern conditions gave aldehyde (XIII). Finally, reductive coupling of aldehyde (XIII) with piperazinone (VI) in the presence of sodium triacetoxyborohydride furnished the title compound.

2 Williams, T.M. (Merck & Co., Inc.); Biaryl inhibitors of prenyl-protein transferase. WO 0075135 .
1 Kohl, N.E.; Nguyen, D.N.; Lobell, R.B.; Williams, T.M.; Heimbrook, D.C.; Buser, C.A.; Huber, H.E.; Stump, C.A.; Graham, S.L.; Potent inhibitors of farnesyltransferase and geranylgeranyltransferase. 221st ACS Natl Meet (April 1 2001, San Diego) 2001, Abst MEDI 56.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VI) 47289 1-(3-chlorophenyl)-2-piperazinone C10H11ClN2O 详情 详情
(VII) 15869 4-bromobenzylamine; (4-bromophenyl)methanamine 26177-44-6 C7H8BrN 详情 详情
(VIII) 14575 Dihydroxyacetone; 1,3-dihydroxyacetone 96-26-4 C3H6O3 详情 详情
(IX) 48637 [1-(4-bromobenzyl)-2-sulfanyl-1H-imidazol-5-yl]methanol C11H11BrN2OS 详情 详情
(X) 48638 [1-(4-bromobenzyl)-1H-imidazol-5-yl]methanol C11H11BrN2O 详情 详情
(XI) 48639 4-(Trifluoromethyl)phenylboronic acid C7H6BF3O2 详情 详情
(XII) 48640 (1-[[4'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methyl]-1H-imidazol-5-yl)methanol C18H15F3N2O 详情 详情
(XIII) 48641 1-[[4'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-carbaldehyde C18H13F3N2O 详情 详情
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