[CH2:1]([N:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)[CH3:2].F[C:10]1[CH:11]=[CH:12][C:13]([N+:17]([O-:19])=[O:18])=[C:14]([NH2:16])[CH:15]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:10]2[CH:11]=[CH:12][C:13]([N+:17]([O-:19])=[O:18])=[C:14]([NH2:16])[CH:15]=2)[CH2:5][CH2:4]1)[CH3:2]A mixture of 1-ethyl-piperazine (1.2 mL, 9.6 mmol), 5-fluoro-2-nitro-phenylamine (1 g, 6.4 mmol), DIPEA (1.24 g, 9.6 mmol) in DMF (15 mL) was heated at 80° C. overnight. The reaction mixture was poured into ice water and extracted with EtOAc. The combined extract was washed with brine, dried over anhydrous Na2SO4, and concentrated to obtain a crude product, which was purified by flash chromatography on silica to afford the title compound (1 g, yield: 63%). ESI-MS: 251 [M+H]+.
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