COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[CH:23]=[CH:22][C:21]([N:24]([C:33]5[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=5)[C:25]([C:27]5([C:30]([NH2:32])=[O:31])[CH2:29][CH2:28]5)=[O:26])=[CH:20][CH:19]=4)=[C:11]3[C:10]([CH3:40])=[N:9]2)=CC=1.C(O)(C(F)(F)F)=O>C([O-])([O-])=O.[Na+].[Na+]>[F:39][C:36]1[CH:37]=[CH:38][C:33]([N:24]([C:21]2[CH:22]=[CH:23][C:18]([O:17][C:16]3[CH:15]=[CH:14][N:13]=[C:12]4[NH:8][N:9]=[C:10]([CH3:40])[C:11]=34)=[CH:19][CH:20]=2)[C:25]([C:27]2([C:30]([NH2:32])=[O:31])[CH2:28][CH2:29]2)=[O:26])=[CH:34][CH:35]=1A 40 mL vial was charged with N-(4-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide (90 mg, 0.11 mmol) and TFA (2.0 mL). The reaction mixture was heated to 65° C. under nitrogen for 2 hours, the diluted with saturated Na2CO3 (15 mL) and extracted with EtOAc. The organic layer was dried over sodium sulfate, filtered and concentrated. The crude material was purified by preparative TLC (0.5 mm) eluting with EtOAc/MeOH (9:1) to provide the product as a white solid. 1H NMR (CDCl3, 400 MHz) δ 8.22 (d, J=5.5 Hz, 1H), 7.71 (d, J=9.0 Hz, 2H), 7.56 (m, 2H), 7.22 (d, J=9.0 Hz, 2H), 7.06 (t, J=9.0 Hz, 2H), 6.27 (d, J=5.5 Hz, 1H), 2.68 (s, 3H), 1.64 (s, 4H). LRMS (esi pos) m/e 446 (M+1).
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