[Cl:1][C:2]1[C:3]([CH:8]([C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)[N:9]2C(=O)C3C(=CC=CC=3)C2=O)=[N:4][CH:5]=[CH:6][N:7]=1.NN.CCO>C(Cl)Cl>[Cl:1][C:2]1[C:3]([CH:8]([NH2:9])[C:20]2[CH:21]=[CH:22][C:23]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:24][CH:25]=2)=[N:4][CH:5]=[CH:6][N:7]=1A solution of 2-[(3-chloropyrazin-2-yl)-(4-phenoxyphenyl)-methyl]-isoindole-1,3-dione (1.04 g, 0.0023 mol) and anhydrous hydrazine (0.247 mL, 0.0078 mol) in DCM (8.8 mL)/EtOH (6 mL) was stirred at rt overnight. The white precipitate (phthalic hydrazide) was filtered and washed with DCM. The filtrate was collected and concentrated in vacuo and purified by flash column chromatography using 10%-30% EtOAc in hexanes to afford 570 mg of the title compound as an orange oily solid. 1H NMR (400 MHz, CDCl3): δ 2.38 (br. s., 2H), 5.54 (s, 1H), 6.89-7.01 (m, 4H), 7.09 (t, J=7.45 Hz, 1H), 7.27-7.36 (m, 4H), 8.26 (d, J=2.27 Hz, 1H), 8.53 (d, J=2.53 Hz, 1H). MS (ES+): m/z 294.72 (90) [MH+]. HPLC: tR=2.15 min (Open Lynx, polar—5 min).
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