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【结 构 式】

【分子编号】53052

【品名】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

【CA登记号】n/a

【 分 子 式 】C20H25F3N2

【 分 子 量 】350.4271896

【元素组成】C 68.55% H 7.19% F 16.26% N 7.99%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(XVI)

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.

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:(XV)

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

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