I([O-])(=O)(=O)=O.[Na+].[OH:7][CH:8]([C:11]1[N:16]=[C:15]([C:17]2[N:22]=[CH:21][C:20]3[CH:23]=[N:24][N:25]([C:26]4[N:31]=[C:30]([N:32]5[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]5)[CH:29]=[CH:28][CH:27]=4)[C:19]=3[CH:18]=2)[CH:14]=[N:13][CH:12]=1)CO>O.O1CCCC1>[CH:8]([C:11]1[N:16]=[C:15]([C:17]2[N:22]=[CH:21][C:20]3[CH:23]=[N:24][N:25]([C:26]4[N:31]=[C:30]([N:32]5[CH2:33][CH2:34][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:36][CH2:37]5)[CH:29]=[CH:28][CH:27]=4)[C:19]=3[CH:18]=2)[CH:14]=[N:13][CH:12]=1)=[O:7]A solution of sodium periodate (260 mg 1.22 mmol) in 5 ml of water was added to a solution of tert-butyl 4-[6-[6-[6-(1,2-dihydroxyethyl)pyrazin-2-yl]pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperazine-1-carboxylate (315 mg, 0.61 mmol) in 25 ml of tetrahydrofuran and 5 ml of water. The mixture was stirred for 24 hours, concentrated, the residue partitioned between ethyl acetate and water, the organic extracts were washed with water, brine, dried over sodium sulfate and concentrated. The residue was purified on 12 g silica gel column eluting with ethyl acetate gradient in heptane to afford 245 mg (83%). MS (ESI) m/z: 505.2 [M+H2O+H]+.
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