Cl[C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][N:15]=3)[NH:10][N:9]=2)[CH:5]=[CH:4][CH:3]=1.[NH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>CN1C(=O)CCC1.CCOC(C)=O>[N:17]1([C:2]2[N:7]=[C:6]([C:8]3[C:16]4[C:11](=[N:12][CH:13]=[CH:14][N:15]=4)[NH:10][N:9]=3)[CH:5]=[CH:4][CH:3]=2)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1A mixture of 3-(6-chloro-2-pyridyl)-1H-pyrazolo[3,4-b]pyrazine (150 mg, 0.6476 mmol) and piperazine (167.4 mg, 1.943 mmol) in NMP (1.5 mL) was heated in microwave at 150° C. for a total of 1.5 h. Mixture cooled to ambient, diluted with EtOAc and washed with sat. NaHCO3 solution (1×), water (2×), brine (1×), dried (MgSO4), filtered and concentrated in vacuo. Crude product purified by ISCO companion (24 g SiO2, 0.5 to 10% MeOH (containing 10% ammonium hydroxide), pure fractions combined and concentrated in vacuo. Product re-dissolved in MeCN/H2O and freeze-dried to leave title compound as a yellow solid (20 mg, 11%). 1H NMR (DMSO-d6) δ2.82 (t, 4H), 3.56 (t, 4H), 6.85 (d, 1H), 7.69 (t, 1H), 7.77 (d, 1H), 8.65 (d, 1H) and 8.73 (d, 1H). ES+281.9.
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