[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]2[N:8]3[CH2:14][CH2:13][CH2:12][C:9]3=[N:10][N:11]=2)[CH2:2]1.Cl[C:16]1[N:21]=[C:20]([NH2:22])[C:19]([N+:23]([O-:25])=[O:24])=[CH:18][CH:17]=1.C(N(CC)CC)C>C(#N)C>[N:10]1[N:11]=[C:7]([CH:3]2[CH2:4][CH2:5][CH2:6][N:1]([C:16]3[N:21]=[C:20]([NH2:22])[C:19]([N+:23]([O-:25])=[O:24])=[CH:18][CH:17]=3)[CH2:2]2)[N:8]2[CH2:14][CH2:13][CH2:12][C:9]=12To a solution of 3-(piperidin-3-yl)-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazole (900 mg, 4.68 mmol) in acetonitrile (50 mL) was added 6-chloro-3-nitropyridin-2-amine (730 mg, 4.2 mmol) and triethylamine (1.42 g, 14.04 mmol) at room temperature under a nitrogen atmosphere. The reaction mixture was stirred for 30 min at reflux, then allowed to cool down to room temperature and stirred for 16 h. The solvent was removed under reduced pressure and the resulting residue was partitioned between water and ethyl acetate. The organics were dried over sodium sulfate, concentrated under reduced pressure and purified via column chromatography to afford the title compound (1.0 g, 64.9%). MS (ES+) (M+H) 330.33; LCMS retention time: 2.85 min (Method S).
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