Water → HCID 58997014, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-{3-[1-(4-chloro-phenyl)-1-methyl-ethyl]-pyridin-2-ylmethyl-N-(3,5-dimethyl-pyridin-2-ylmethyl)-butane-1,4-diamine (0.200 g, 0.444 mmol) in dry MeOH (4 mL), at 0° C., was added NaOAc (0.106 g, 1.29 mmol) and BrCN (0.063 g, 0.59 mmol). The mixture was stirred at 0° C. for 30 min, then at room temperature for 2 h. Water (10 mL) was added, and the mixture was extracted with CH2Cl2 (3×20 mL). The organic extracts were combined and dried over anhydrous Na2SO4. After filtration the solvent was removed by evaporation under vacuum. The residue was purified by flash chromatography on a silica gel column (100:5:2 CH2Cl2/MeOH/NH4OH), affording a pale yellow oil (0.13 g, 62%). 1H NMR (CDCl3) δ 1.35-1.45 (m, 4H), 1.65 (s, 6H), 1.99 (s, 3H), 2.25 (s, 3H), 2.32-2.40 (m, 2H), 2.62-2.70 (m, 2H), 3.04 (s, 2H), 3.22 (s, 2H), 7.02 (d, 2H, J=8.1 Hz), 7.15-7.28 (m, 4H), 7.91 (d, 1H, J=7.8 Hz), 8.13 (s, 1H), 8.48 (s, br. 1H), 8.57 (d, 1H, J=3.9 Hz). ES-MS m/z 476 (M+H).

Provenance & Evidence