1-(4-Aminoquinazoline-7-ylmethyl)-3-propyl-piperazine-2-one → 1-[4-(4-Aminoquinazoline-7-ylmethyl)-3-oxo-2-propyl-piperazine-1-yl]-3-(5-chloro-thiophen-2-yl)-propane-1,3,dione
反応式
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][CH2:17][NH:16][CH:15]([CH2:19][CH2:20][CH3:21])[C:14]3=[O:22])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.C([O:27][C:28](=O)[CH2:29][C:30]([C:32]1[S:33][C:34]([Cl:37])=[CH:35][CH:36]=1)=[O:31])(C)(C)C>N1C=CC=CC=1>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][CH2:17][N:16]([C:28](=[O:27])[CH2:29][C:30]([C:32]4[S:33][C:34]([Cl:37])=[CH:35][CH:36]=4)=[O:31])[CH:15]([CH2:19][CH2:20][CH3:21])[C:14]3=[O:22])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1参加物
4
反応物 2
生成物 1
試薬・触媒・溶媒 1
実験手順
The titled compound is prepared by a modification of a procedure published by Witzeman and Nottingham. (J. Org. Chem. 1991, 56, 1713.). 1-(4-Aminoquinazoline-7-ylmethyl)-3-propyl-piperazine-2-one (0.299 g, 1 mmol) and 3-(5-chloro-thiophen-2-yl)-3-oxo-propionic acid tert-butyl ester (0.287 g, 1.1 mmol) are dissolved in 10 ml of pyridine. The flask containing the resulting solution is placed in an oil bath preheated to 125° C. The reaction is heated with stirring under a stream of nitrogen gas for one hour until most of the pyridine had evaporated. The remaining pyridine is evaporated in vacuo. The residue is purified by flash column chromatography eluting with a gradient of 5% CH3OH/H2CCl2 to 10% CH3OH/H2CCl2 to provide the product (0.48 g, 0.98 mmol). The product could be recrystallized from CH2Cl2/hexane to yield a yellow solid. M.P. 120-5° C. (dec). MS (ion spray) m/z 486, (M+H).