[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C@H:13]([CH3:14])[CH2:12][CH2:11][C@H:10]([C:15]([N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[O:16])[CH2:9]2)[CH:5]=[CH:4][C:3]=1[N+:22]([O-])=O.[H][H]>C(O)C.[Pd]>[NH2:22][C:3]1[CH:4]=[CH:5][C:6]([N:8]2[C@H:13]([CH3:14])[CH2:12][CH2:11][C@H:10]([C:15]([N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[O:16])[CH2:9]2)=[N:7][C:2]=1[NH2:1]A solution of cis-(1-(6-amino-5-nitropyridin-2-yl)-6-methylpiperidin-3-yl)(pyrrolidin-1-yl)methanone (500 mg, 1.50 mmol) in ethanol (20 mL) was added to a suspension of 10% palladium-on-carbon (250 mg) in ethanol under a nitrogen atmosphere. The suspension was hydrogenated using a balloon filled with hydrogen gas for 2 h at room temperature. The mixture was filtered through Celite and the filtrate was used for the next step without further purification.
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