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【结 构 式】 
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【分子编号】35755 【品名】ethyl 5-[[benzyl(3-pyridinyl)amino]methyl]-2'-methyl[1,1'-biphenyl]-2-carboxylate 【CA登记号】 |
【 分 子 式 】C29H28N2O2 【 分 子 量 】436.5536 【元素组成】C 79.79% H 6.46% N 6.42% O 7.33% |
合成路线1
该中间体在本合成路线中的序号：(VI)Condensation of 3-aminopyridine (I) with benzaldehyde (II) in refluxing toluene with azeotropic removal of water produced imine (III), which was reduced to amine (IV) using ethanolic NaBH4. Subsequent alkylation of (IV) with methyl 4-bromomethyl-2-(2-methylphenyl)benzoate (V) in the presence of n-BuLi in cold THF yielded the tertiary amine (VI). Basic hydrolysis of the ester group of (VI), followed by EDC-promoted coupling of the resulting carboxylic acid (VII) with L-methionine methyl ester (VIII) afforded amide (IX). The title compound was finally obtained by saponification of the methyl ester group of (IX) by means of LiOH.
| 【1】 Wang, L.; Barr, K.J.; O'Connor, S.; et al.; Second-generation peptidomimetic inhibitors of protein farnesyltransferase demonstrating improved cellular potency and significant in vivo efficacy. J Med Chem 1999, 42, 18, 3701. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 33327 | 3-Pyridinylamine; 3-Aminopyridine; 3-Pyridinamine | 462-08-8 | C5H6N2 | 详情 | 详情 |
| (II) | 10498 | Benzaldehyde;Benzoic aldehyde;Phenylmethanal | 100-52-7 | C7H6O | 详情 | 详情 |
| (III) | 35752 | N-[(Z)-benzylidene]-N-(3-pyridinyl)amine; N-[(Z)-benzylidene]-3-pyridinamine | C12H10N2 | 详情 | 详情 | |
| (IV) | 35753 | N-benzyl-N-(3-pyridinyl)amine; N-benzyl-3-pyridinamine | C12H12N2 | 详情 | 详情 | |
| (V) | 35754 | ethyl 5-(bromomethyl)-2'-methyl[1,1'-biphenyl]-2-carboxylate | C17H17BrO2 | 详情 | 详情 | |
| (VI) | 35755 | ethyl 5-[[benzyl(3-pyridinyl)amino]methyl]-2'-methyl[1,1'-biphenyl]-2-carboxylate | C29H28N2O2 | 详情 | 详情 | |
| (VII) | 35756 | 5-[[benzyl(3-pyridinyl)amino]methyl]-2'-methyl[1,1'-biphenyl]-2-carboxylic acid | C27H24N2O2 | 详情 | 详情 | |
| (VIII) | 17950 | D-Methionine methyl ester; methyl (2S)-2-amino-4-(methylsulfanyl)butanoate hydrochloride | 21691-49-6 | C6H13NO2S | 详情 | 详情 |
| (IX) | 35757 | methyl (2S)-2-[[(5-[[benzyl(3-pyridinyl)amino]methyl]-2'-methyl[1,1'-biphenyl]-2-yl)carbonyl]amino]-4-(methylsulfanyl)butanoate | C33H35N3O3S | 详情 | 详情 |