[NH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][N:4]=1)[NH2:2].[C:12]([C:14]1[C:19]([F:20])=[CH:18][C:17]([C:21](=[CH:26]N(C)C)[C:22](OC)=[O:23])=[C:16]([CH3:30])[CH:15]=1)#[N:13].Cl.C(N(C(C)C)C(C)C)C>O.CC(O)C>[C:12]([C:14]1[C:19]([F:20])=[CH:18][C:17]([C:21]2[CH:26]=[N:2][N:1]([C:3]3[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][N:4]=3)[C:22]=2[OH:23])=[C:16]([CH3:30])[CH:15]=1)#[N:13]Combined 6-hydrazinylnicotinic acid (0.73 g, 4.77 mmol), methyl 2-(4-cyano-5-fluoro-2-methylphenyl)-3-(dimethylamino)acrylate (1.375 g, 5.24 mmol), 2-propanol (18 mL), and 0.5M aqueous hydrochloric acid (11.44 mL, 5.72 mmol). After 2 hours, N-ethyl-N-isopropylpropan-2-amine (4.15 mL, 23.83 mmol). After an hour the reaction mixture was diluted with water and washed with IPAc twice. The aqueous phase was acidified to ˜pH=3.5 and stirred for 30 minutes to give a solid which was collected by filtration, washed with water, ethanol, and heptanes, and dried overnight under vacuum to give the title compound (1.20 g, 74%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.41 (s, 3 H) 7.74 (d, J=7.07 Hz, 1 H) 7.91 (d, J=11.62 Hz, 1 H) 8.26 (s, 1 H) 8.37-8.47 (m, 1 H) 8.47-8.56 (m, 1 H) 8.96 (dd, J=2.15, 0.88 Hz, 1 H). ESI-MS m/z [M+H]+ 339.2.
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