Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]2[N:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[N:13]=[C:14]([CH3:15])[C:3]=12.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:15][C:14]1[C:3]2[C:4](=[N:5][C:6]3[C:11]([C:2]=2[N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[N:13]=1A solution of 4-chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline (1.47 g, 5.00 mmol), morpholine (0.87 g, 10.0 mmol) and potassium carbonate (1.38 g, 10.0 mmol) in N,N-dimethylformamide (20 mL) was heated under reflux at 100° C. for 12 hours. The solution was cooled to room temperature, and concentrated under reduced pressure. The residue was poured into water and organic matter was extracted with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The residue thus obtained was purified by basic silica gel column chromatography (hexane:chloroform=3:1) to give the title compound (0.63 g, 36% yield).
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