[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[N:3]1[CH:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:22]=[CH:21][N:20]=[C:19]([C:23]([OH:25])=O)[CH:18]=2)[CH2:13][CH2:12]1.[NH:26]1[C:34]2[C:29](=[C:30]([NH2:35])[CH:31]=[CH:32][CH:33]=2)[CH:28]=[N:27]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[NH:26]1[C:34]2[C:29](=[C:30]([NH:35][C:23]([C:19]3[CH:18]=[C:17]([N:14]4[CH2:15][CH2:16][CH:11]([N:3]5[C:4]6[C:5](=[N:6][CH:7]=[CH:8][CH:9]=6)[NH:10][C:2]5=[O:1])[CH2:12][CH2:13]4)[N:22]=[CH:21][N:20]=3)=[O:25])[CH:31]=[CH:32][CH:33]=2)[CH:28]=[N:27]1100 mg (0.29 mmol) 6-[4-(2-oxo-2,3-dihydroimidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid and 39 mg (0.29 mmol) 1H-indazole-4-ylamine in 87 mL (0.62 mmol) TEA and 1.5 mL DMF were combined with 104 mg (0.32 mmol) TBTU and stirred overnight at RT. Then the reaction mixture was purified by preparative HPLC-MS. The product-containing fractions were combined and freeze-dried.
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