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A solution of 1,1′-carbonyldiimidazole (0.1054 g, 0.65 mmol), 2-aminoimidazole sulfate (0.0859 g, 0.65 mmol), and DIPEA (0.45 mL, 2.60 mmol) in DMF (7 mL) was stirred at room temperature for 4 hours. (3,5-Dimethyl-pyridin-2-ylmethyl)-(3-isopropyl-pyridin-2-ylmethyl)-piperidin-4-yl-amine (0.2301 g, 0.65 mmol) was added and stirred at 60° C. for 22 hours, then concentrated. Saturated NaHCO3 (15 mL) was added and extracted with CH2Cl2 (3×30 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. Purification of the crude material by column chromatography on silica gel (50:1:1 CH2Cl2-MeOH—NH4OH) followed by radial chromatography on silica (100:1:1 CH2Cl2-MeOH—NH4OH) provided 30.2 mg (10%) COMPOUND 348 as a yellow solid. 1H NMR (CDCl3) δ 0.93 (d, 6H, J=9.0 Hz), 1.61-1.72 (m, 2H), 1.93 (d, 2H, J=11.1 Hz), 2.16 (s, 3H), 2.28 (s, 3H), 2.68-2.79 (m, 4H), 3.80 (d, 4H, J=18.3 Hz), 4.33 (d, 2H, J=12.9 Hz), 6.70 (s, 2H), 7.12-7.16 (m, 1H), 7.24 (s, 1H), 7.50 (d, 1H, J=7.5 Hz), 8.18 (s, 1H), 8.32 (d, 1H, J=4.5 Hz). 13C NMR (CDCl3) 18.29, 18.46, 23.60, 27.39, 27.59, 44.78, 54.32, 57.40, 123.16, 132.26, 133.21, 133.85, 139.06, 144.40, 145.46, 146.07, 146.64, 154.49, 155.70, 156.31. ES-MS m/z 463.1 (M+H). Anal. Calcd. for C26H35N7O.0.3CH2Cl2: C, 64.85; H, 7.37; N, 20.13. Found: C, 64.72; H, 7.63; N, 19.74.
