[CH2:1]([N:8]([CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[C:9](=[O:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:19]1[N:24]=[CH:23][C:22]([C:25]2[NH:34][C:33](=[O:35])[C:32]3[C:27](=[CH:28][C:29]([O:38][CH3:39])=[CH:30][C:31]=3[O:36][CH3:37])[N:26]=2)=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([N:8]([CH:12]1[CH2:17][CH2:16][N:15]([C:19]2[CH:20]=[CH:21][C:22]([C:25]3[NH:34][C:33](=[O:35])[C:32]4[C:27](=[CH:28][C:29]([O:38][CH3:39])=[CH:30][C:31]=4[O:36][CH3:37])[N:26]=3)=[CH:23][N:24]=2)[CH2:14][CH2:13]1)[C:9](=[O:11])[CH3:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1To a solution of N-benzyl-N-(piperidin-4-yl)acetamide (1.5 g, 6.3 mmol) and 2-(6-chloropyridin-3-yl)-5,7-dimethoxyquinazolin-4(3H)-one (1.0 g, 3.2 mmol) in DMF (15 mL) was added K2CO3 (0.875 g, 6.3 mmol) and the reaction was heated at reflux temperature overnight. The resulting mixture was concentrated in vacuo and purified by flash chromatography on silica gel, eluting with 1% to 10% MeOH/CH2Cl2, to afford the title compound (0.500 g, 30%) as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 11.84 (s, 1H), 8.86 (s, 1H), 8.22 (d, J=9.2 Hz, 1H), 7.33-7.37 (m, 1H), 7.14-7.27 (m, 4H), 6.88-6.96 (m, 1H), 6.66 (d, J=1.5 Hz, 1H), 6.46 (d, J=1.5 Hz, 1H), 4.44-4.58 (m, 4.5H), 4.10-4.20 (m, 0.5H), 3.87 (s, 3H), 3.83 (s, 3H), 2.86-2.98 (m, 2H), 2.25 (s, 1.5H), 1.95 (s, 1.5H), 1.45-1.77 (m, 4H). ESI/APCI MS m/z 514 [M+H]+.
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