[C:1]([O:5][C:6](=[O:19])[CH2:7][N:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C:10]([C:17]#[N:18])=[N:9]1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:21][OH:22].CCN(CC)CC>CCO>[C:1]([O:5][C:6](=[O:19])[CH2:7][N:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C:10]([C:17](=[NH:18])[NH:21][OH:22])=[N:9]1)([CH3:4])([CH3:2])[CH3:3]A mixture of (3-cyano-pyrazolo[3,4-b]pyridin-1-yl)-acetic acid tert-butyl ester, hydroxylamine hydrochloride (8.28 g) and Et3N (22.6 mL) in EtOH (120 mL) was heated over night under N2 at 65° C. The resultant mixture was cooled to room temperature, filtered and the collected solid was washed with H2O (100 mL) and Et2O (50 mL×2) to afforded [3-(N-hydroxycarbamimidoyl)-pyrazolo[3,4-b]pyridin-1-yl]-acetic acid tert-butyl ester.
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