(1-[[4'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methyl]-1H-imidazol-5-yl)methanol -Drug Synthesis Database

【结构式】

【分子编号】48640

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

【CA登记号】

【分子式】C₁₈H₁₅F₃N₂O

【分子量】332.3251896

【元素组成】C 65.06% H 4.55% F 17.15% N 8.43% O 4.81%

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：(XII)

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.

参考文献中间体

合成目标

【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

Extended Information