[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[CH:22]([CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:21]3[C:12]([C:13]4[CH:14]=[CH:15][C:16]([C:28](O)=[O:29])=[N:17][C:18]=4[CH2:19][CH2:20]3)=[N:11]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[CH3:31][NH:32][C@@H:33]1[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>ClCCl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[CH:22]([CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:21]3[C:12]([C:13]4[CH:14]=[CH:15][C:16]([C:28]([N:32]([CH3:31])[C@@H:33]5[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34]5)=[O:29])=[N:17][C:18]=4[CH2:19][CH2:20]3)=[N:11]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]In a dried reaction flask, 2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-pyrazolo[3,4-f]quinoline-7-carboxylic acid (0.421 g, 1.0 mmol), (R)—N,1-dimethylpyrrolidine-3-amine (0.308 g, 2.697 mmol), DIEA (0.4 mL, 2.30 mmol), and HATU (0.836 g, 2.2 mmol) were added to a mixed solvent of DMF (3 mL) and dichloromethane (6 mL). The mixture was stirred at room temperature for 18 hr and was concentrated under reduced pressure. Water was added to the residue. The mixture was washed with water, and was purified by a preparative chromatography to produce a purified product as pale yellow solid (80 mg) in 15.5% yield.
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