Reaction Steps
To a solution of 3-amino-4-(3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-benzoic acid methyl ester (0.61 g, 1.42 mmol) in THF (14 mL) was added LiBH4 (430 mg, 19.74 mmol) and the mixture was heated to reflux overnight. The mixture was cooled to room temperature, diluted with 1.0 N NaOH (20 mL) and extracted with CH2Cl2 (5×30 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by radial chromatography on silica gel (2 mm plate, 20:1:1 CH2Cl2—CH3OH—NH4OH) provided 0.220 g (37%) of COMPOUND 59 as a white solid. 1H NMR (CDCl3) δ 1.23 (br s, 1H), 1.47-1.72 (m, 3H), 1.88-1.95 (m, 1H), 2.04-2.18 (m, 2H), 2.35 (s, 6H), 3.32 (s, 2H), 3.73 (dd, 2H, J=11.7, 3.0 Hz), 4.26 (d, 2H, J=3.3 Hz), 4.53 (br s, 2H), 6.03 (s, 1H), 6.07 (d, 1H, J=7.8 Hz), 6.48 (d, 1H, J=7.2 Hz), 6.86 (dd, 2H, J=7.8, 4.8 Hz), 7.15 (d, 2H, J=7.5 Hz), 8.33 (d, 2H, J=3.9 Hz). 13C NMR (CDCl3) δ 19.44, 25.02, 32.92, 60.69, 65.60, 68.25, 112.98, 115.09, 122.09, 122.80, 129.96, 131.38, 138.18, 140.42, 146.89, 147.51, 161.18; ES-MS m/z 403 (M+H). Anal. Calcd. For C25H30N4O.1.0H2O: C, 71.40; H, 7.67; N, 13.32. Found: C, 71.31; H, 7.55; N, 13.22.
