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3-(5-Chloro-2-oxo-2H-[1,2']bipyridinyl-5'-ylmethyl)-4-(4-cyano-phenyl)-3,4,6,7-tetrahydro-imidazo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester (0.27 g, 0.50 mmol) was dissolved in EtOAc, cooled to 0° C., degassed with Ar, and saturated with anh. HCl gas. The solution was concentated in vacuo and the diastereomers separated using a Chiralcel OD column (25 cm×2 cm, 10/90-0/100 Hexane/EtOH with 0.1% DEA, flow 5.0 mL/min) followed by enantiomer seperation using a Delta Pak C18 column (0-100% H2O (0.1% NH4HCO3)/CH3CN) to give the title compound. 1H NMR (CDCl3); δ 8.01-7.96 (m, 3H), 7.60 (d, 2H, J=8 Hz), 7.54 (s, 1H), 7.37-7.30 (m, 2H), 7.27-7.21 (m, 3H), 6.61 (d, 1H, J=10 Hz), 4.85 (d, 1H, J=16 Hz), 4.79 (s, 1H), 4.45 (s, 1H, J=16 Hz), 3.05-3.01 (m, 2H), 2.80-2.77 (m, 2H).

1. customdegassed with Ar
2. customthe diastereomers separated
3. customfollowed by enantiomer seperation