[CH3:1][N:2]([CH2:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].Cl[C:18]1[CH:23]=[CH:22][N:21]=[CH:20]C=1.CC[N:26](C(C)C)C(C)C>CC(O)C.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[CH3:1][N:2]([CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][N:26]=2)[CH2:13][CH2:12]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:6])[CH3:7]tert-Butyl methyl(piperidin-4-ylmethyl)carbamate (1.4 mmol, 1.0 eq) and 4-chloropyridine (4.2 mmol, 3.0 eq) were dissolved in 2-propanol (5 ml) and DIPEA (7.0 mmol. 5.0 eq) and refluxed for 16 hours. After monitoring by TLC, the reaction solution was diluted with ethyl acetate and sat. sodium hydrogen carbonate solution and the phases were separated. The aqueous phase was washed with ethyl acetate. The combined organic phases were dried over magnesium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, ethyl acetate:ethanol 10:1+ammonia solution). Yield: 51%
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