[NH2:1][OH:2].Cl.C([O-])([O-])=O.[K+].[K+].[O:10]1[C:18]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[CH:12]=[C:11]1[C:19]#[N:20]>O.CCO>[OH:2][NH:1][C:19]([C:11]1[O:10][C:18]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[CH:12]=1)=[NH:20]A solution of NH2OH.HCl (1.22 g, 17.5 mmol) and K2CO3 (1.21 g, 8.75 mmol) in H2O (3 mL) was added to a stirred solution of furo[3,2-c]pyridine-2-carbonitrile (1.26 g, 8.75 mmol) in EtOH (6 mL). The reaction was heated to 70° C. for 2 h, before being concentrated in vacuo. The remainder was partitioned between EtOAc and H2O. The aqueous phase was extracted with EtOAc (8×), then the combined organic extracts were washed with brine, back-extracting with EtOAc (4×). The combined organic extracts were dried (MgSO4), filtered, and concentrated to give the title compound: m/z (ES+)=178.0 [M+H]+.
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