[NH2:1][C:2]([C:4]1[CH:8]=[C:7]([C:9]2[C:14]([F:15])=[CH:13][C:12]([C:16]([OH:19])([CH3:18])[CH3:17])=[CH:11][C:10]=2[F:20])[S:6][C:5]=1[NH:21][C:22]1[N:27]=[C:26]([CH2:28][N:29]2[CH:33]=[C:32]([C:34]([O-])=[O:35])[N:31]=[N:30]2)[CH:25]=[CH:24][CH:23]=1)=[O:3].[K+].C1C=CC2N(O)N=[N:44][C:42]=2C=1.C(Cl)CCl.Cl.CN.CCN(C(C)C)C(C)C>CN(C=O)C.O>[NH2:1][C:2]([C:4]1[CH:8]=[C:7]([C:9]2[C:10]([F:20])=[CH:11][C:12]([C:16]([OH:19])([CH3:17])[CH3:18])=[CH:13][C:14]=2[F:15])[S:6][C:5]=1[NH:21][C:22]1[N:27]=[C:26]([CH2:28][N:29]2[CH:33]=[C:32]([C:34]([NH:44][CH3:42])=[O:35])[N:31]=[N:30]2)[CH:25]=[CH:24][CH:23]=1)=[O:3]Potassium 1-{[6-({3-(aminocarbonyl)-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)pyridin-2-yl]methyl}-1H-1,2,3-triazole-4-carboxylate (111 mg, 0.20 mmol), HOBT (62 mg, 0.40 mmol), EDC (77 mg, 0.40 mmol), and methylamine hydrochloride (41 mg, 0.60 mmol) were combined in DMF (5.0 mL), and DIEA (105 μL, 0.60 mmol) was added. The reaction was stirred at room temperature overnight. The solution was diluted with water to precipitate an off-white solid that was collected by filtration, washed (water, MeOH, CH2Cl2), and dried to yield the title compound. 1H NMR (600 MHz, DMSO-d6) δ 12.15 (s, 1H), 8.55 (s, 1H), 8.30 (q, 1H), 7.86 (s, 1H), 7.73-7.66 (m, 2H), 7.36 (s, 1H), 7.21 (d, 2H), 7.03 (d, 1H), 6.80 (d, 1H), 5.71 (s, 2H), 5.27 (s, 1H), 2.66 (d, 3H), 1.42 (s, 6H). Calc'd for C24H24F2N7O3S [M+H]+ 528. found 528.
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