[C:1]([C:4]1[C:13]([N:14]2[CH2:19][CH2:18][N:17]([CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[CH2:16][CH2:15]2)=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[C:6]([Cl:26])[CH:5]=1)(=O)[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:33].[Na+]>CO.C(#N)C.O1CCCC1>[NH2:33][CH:1]([C:4]1[C:13]([N:14]2[CH2:19][CH2:18][N:17]([CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[CH2:16][CH2:15]2)=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[C:6]([Cl:26])[CH:5]=1)[CH3:2]A mixture of 2-[4-(7-acetyl-5-chloroquinolin-8-yl)piperazin-1-yl]-N,N-dimethylacetamide (0.019 g, 0.051 mmol) and ammonium acetate (0.0391 g, 0.507 mmol) in methanol (0.3 mL) and acetonitrile (0.3 mL) was heated at 65° C. in a sealed tube for 1 hour. After cooling to room temperature, to the resulting mixture was added 1.0 M sodium cyanoborohydride in tetrahydrofuran (0.12 mL). The reaction was heated at 65° C. overnight. The mixture was cooled to room temperature, quenched with sat. NaHCO3 solution, extracted with dichloromethane, dried over MgSO4 and concentrated to give the desired product. LCMS calculated for C19H27ClN5O (M+H)+: m/z=376.2; Found: 376.2.
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