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【结 构 式】

【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%

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:(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
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