4-[4-(trifluoromethyl)phenyl]benzaldehyde -Drug Synthesis Database

【结构式】

【分子编号】53051

【品名】4-[4-(trifluoromethyl)phenyl]benzaldehyde

【CA登记号】n/a

【分子式】C₁₄H₉F₃O

【分子量】250.2200696

【元素组成】C 67.2% H 3.63% F 22.78% O 6.39%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(XIV)

Suzuki coupling between 4-bromobenzaldehyde (XII) and 4-trifluoromethylbenzeneboronic acid (XIII) produced the biphenyl compound (XIV). The reductive amination of aldehyde (XIV) with N,N-diethyl ethylenediamine (XV) gave diamine (XVI) (1). This was finally coupled with the intermediate carboxylic acid (XI) to afford the title amide.

参考文献中间体

合成目标

【1】 Smith, S.A.; Inhibition of lipoprotein-associated phospholipase A2 - A novel approach for the treatment of atherosclerosis. 11th RSC-SCI Med Chem Symp (Sept 9 2001, Cambridge) 2001, Abst .
【2】 Ife, R.J.; Leach, C.A.; Smith, S.A.; Pinto, I.L.; Hickey, D.M.B.; Fenwick, A.E. (GlaxoSmithKline plc); Pyrimidinone cpds.. EP 1175408; WO 0066567 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XI)	53050	2-[2-[(4-fluorobenzyl)sulfanyl]-5-[(1-methyl-1H-pyrazol-4-yl)methyl]-4-oxo-1(4H)-pyrimidinyl]acetic acid	n/a	C₁₈H₁₇FN₄O₃S	详情	详情
(XII)	22231	4-Bromobenzaldehyde	1122-91-4	C₇H₅BrO	详情	详情
(XIII)	48639	4-(Trifluoromethyl)phenylboronic acid		C₇H₆BF₃O₂	详情	详情
(XIV)	53051	4-[4-(trifluoromethyl)phenyl]benzaldehyde	n/a	C₁₄H₉F₃O	详情	详情
(XV)	12420	N-(2-Aminoethyl)-N,N-diethylamine; N,N-Diethylethylene-diamine; N(1),N(1)-Diethyl-1,2-ethanediamine	100-36-7	C₆H₁₆N₂	详情	详情
(XVI)	53052	N-[2-(diethylamino)ethyl]-N-{[4'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methyl}amine; N~1~,N~1~-diethyl-N~2~-{[4'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methyl}-1,2-ethanediamine	n/a	C₂₀H₂₅F₃N₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XIII)

Suzuki coupling between 4-bromobenzaldehyde (XI) and 4-trifluoromethylbenzeneboronic acid (XII) affords the biphenylyl aldehyde (XIII). This is then reductively aminated with N,N-diethylethylenediamine (XIV) and NaBH4 to produce diamine (XV) (1,3). Finally, coupling between amine (XV) and carboxylic acid (VIII) leads to the title carboxamide

参考文献中间体

合成目标

【1】 The identification of clinical candidate SB-480848: A potent inhibitor of lipoprotein-associated phospholipase A2. Bioorg Med Chem Lett 2003, 13, 6, 1067.
【2】 Ife, R.J.; Leach, C.A.; Hickey, D.M.B.; Pinto, I.L.; Smith, S.A.; Stanway, S.J. (GlaxoSmithKline plc); Pyrimidine-4-one derivs. as LDL-PLA 2 inhibitors. EP 1263740; JP 2003523335; US 2002103213; US 6649619; WO 0160805 .
【3】 Mulholland, K.R.; Ross, A.R.; Smith, G.E.; Slater, G.R. (GlaxoSmithKline plc); Novel processes. WO 0316287 .

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)	63494	2-(2-{[(4-fluorophenyl)methyl]sulfanyl}-4-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-1-yl)acetic acid		C₁₆H₁₅FN₂O₃S	详情	详情
(XI)	22231	4-Bromobenzaldehyde	1122-91-4	C₇H₅BrO	详情	详情
(XII)	48639	4-(Trifluoromethyl)phenylboronic acid		C₇H₆BF₃O₂	详情	详情
(XIII)	53051	4-[4-(trifluoromethyl)phenyl]benzaldehyde	n/a	C₁₄H₉F₃O	详情	详情
(XIV)	12420	N-(2-Aminoethyl)-N,N-diethylamine; N,N-Diethylethylene-diamine; N(1),N(1)-Diethyl-1,2-ethanediamine	100-36-7	C₆H₁₆N₂	详情	详情
(XV)	53052	N-[2-(diethylamino)ethyl]-N-{[4'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methyl}amine; N~1~,N~1~-diethyl-N~2~-{[4'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methyl}-1,2-ethanediamine	n/a	C₂₀H₂₅F₃N₂	详情	详情

Extended Information