FC(F)(F)C(O)=O.[NH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[N:18]3[CH2:19][CH2:20][CH2:21][C:17]3=[CH:16][N:15]=2)[CH2:9]1.C(N(CC)CC)C.Cl[C:30]1[N:35]=[C:34]([NH2:36])[C:33]([N+:37]([O-:39])=[O:38])=[CH:32][CH:31]=1>C(#N)C>[CH:16]1[N:15]=[C:14]([CH:10]2[CH2:11][CH2:12][CH2:13][N:8]([C:30]3[N:35]=[C:34]([NH2:36])[C:33]([N+:37]([O-:39])=[O:38])=[CH:32][CH:31]=3)[CH2:9]2)[N:18]2[CH2:19][CH2:20][CH2:21][C:17]=12To a solution of 3-(piperidin-3-yl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazole trifluoroacetate salt (94 mg) in anhydrous acetonitrile (1.1 mL) at 10° C. was added triethylamine (130 μL, 0.93 mmol). Then 6-chloro-3-nitropyridin-2-amine (39 mg, 0.2 mmol) was added. The reaction mixture was shaken at 80° C. for 2 h and then for 18 h at room temperature. The solvent was removed under reduced pressure and the residue was dissolved in dichloromethane (3 mL). The mixture was washed with a saturated aqueous solution of sodium bicarbonate (1 mL), washed with water (1 mL), washed with brine (1 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified via flash chromatography (0-10% methanol in dichloromethane) to afford 6-(3-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-3-yl)piperidin-1-yl)-3-nitropyridin-2-amine as a yellow oil (60 mg, 82%). MS (ES+) (M+H) 329.2; LCMS retention time: 1.61 minutes (Method L).
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