Reaction Steps
Under N2, To a solution of 2-{[bis-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-5-(methanesulfonylamino-methyl)-benzoic acid methyl ester (0.217 g, 0.450 mmol) in THF (20 mL) was added LiAlH4 (1.0 M in THF, 0.67 mL, 0.67 mmol) at −78° C. After the addition the reaction mixture was brought to room temperature and stirred at room temperature for 30 min. H2O (10 mL) was added, and THF removed. The aqueous residue was extracted with CH2Cl2 (3×20 mL), and the extracts were combined and dried over Na2SO4. After filtration the solvent was removed, and the residue was purified on silica gel column (500:25:1 CH2Cl2/MeOH/NH4OH), affording a white foam (0.165 g, 81%). 1H NMR (CDCl3) δ 2.13 (s, 6H), 2.87 (s, 3H), 3.71 (s, 4H), 3.90 (s, 2H), 4.25 (s, br, 2H), 4.28 (d, 2H, J=6.0 Hz), 4.59 (t, 1H, J=60 Hz), 6.65 (s, br, 1H), 7.06 (dd, 2H, J=4.8, 7.8 Hz), 7.21 (dd, 1H, J=1.5, 7.8 Hz), 7.26-7.31 (m, 2H), 7.38 (d, 2H, J=7.8 Hz), 8.35 (d, 2H, J=4.8 Hz); 13C NMR (CDCl3) δ 18.26, 41.00, 46.84, 57.30, 58.68, 62.79, 122.60, 127.04, 130.68, 131.99, 133.12, 136.72, 137.03, 138.30, 142.35, 146.18, 155.87. ES-MS m/z 455 (M+H). Anal. Calcd. for C24H30N4O3S.0.21CH2Cl2: C, 61.55; H, 6.49; N, 11.86; S, 6.79. Found: C, 61.62; H, 6.58; N, 11.64; S, 6.77.
