Cl[C:2]1[C:11]([CH2:12][OH:13])=[CH:10][C:9]2[C:4](=[C:5]([CH3:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[O:15]=[C:16]1[CH2:21][NH:20][CH2:19][CH2:18][NH:17]1.CCN(C(C)C)C(C)C.CN1C(=O)CCC1>CCOC(C)=O.CCOCC>[OH:13][CH2:12][C:11]1[C:2]([N:20]2[CH2:19][CH2:18][NH:17][C:16](=[O:15])[CH2:21]2)=[N:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH3:14](2-Chloro-8-methylquinolin-3-yl)methanol (250 mg, 1.13 mmol), 2-oxopiperazine (566 mg, 5.66 mmol), DIPEA (1 mL, 5.66 mmol) and NMP (3 mL) were combined in a sealed tube and heated to 140° C. for 24 h. After cooling, the reaction mixture was dissolved in a 1:1 mixture of EtOAc and Et2O (100 mL) and washed with saturated brine (3×25 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. Purification by column chromatography on silica, eluting with 5% MeOH in DCM, afforded the title compound (155 mg, 51%) as a white solid. LCMS (ES+) 272 (M+H)+.
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