A mixture of 2-fluoro-5-((5-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)-1H-imidazol-2-yl)methyl)benzoic acid (Example 104) (50 mg, 0.114 mmol), HOBt (23 mg, 0.171 mmol), DMAP (3 mg, 0.023 mmol), and 2-aminoethanol in pyridine (1 mL) was added EDC (33 mg, 0.171 mmol) and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into H2O and extracted with CH2Cl2 (5 mL, 3 times). The organic layer was dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified by MPLC (MeOH:CH2Cl2=1:100 (v/v) to 1:20 (v/v)) to afford the title compound (34.7 mg, 61%). (300 MHz, CDCl3) δ 2.37 (3H, s), 3.57 (2H, q), 3.79 (2H, t), 4.15 (2H, s), 6.91 (1H, dd), 6.96 (1H, d), 7.04-7.15 (1H, m), 7.20-7.30 (1H, m), 7.37-7.43 (2H, m), 7.80 (1H, dd), 7.85 (1H, dd), 8.04 (1H, d), 8.10 (1H, d), 8.14 (1H, dd), 8.90 (1H, dd), MS (ESI) m/z 482 (MH+).
