3-Pyridinemethanamine → HCID 22615077, compound

Participants

Reaction Conditions

Reaction Steps

3-Methyl-4-oxiranylmethoxy-benzofuran-2-carboxylic acid ethyl ester (500 mg) (Naresh K. Sangwan et al., Eur. J. Med. Chem. (1987), 22(2), 153-6) and 3-picolylamine (1 ml) were dissolved in ethanol (5 ml) and stirred at 70° C. for two hours. The reaction mixture was dissolved in ethyl acetate and washed with saturated ammonium chloride solution and water. The organic solvent was dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by silica gel column chromatography (dichloromethane-MeOH) to afford 4-[2-hydroxy-3-[(pyridin-3-ylmethyl)-amino]-propoxy]-3-methyl-benzofuran-2-carboxylicacid ethyl ester (330 mg) as a white powder. FAB-MS: m/z 385 (MH+); 1H-NMR (CDCl3): δ 1.44 (3H, t, J=7 Hz), 2.70 (3H, s),2.86 (1H, dd, J1=12 Hz, J2=7 Hz),2.97 (1H, dd, J1=12 Hz, J2=3.5 Hz), 3.85 (1H, d, J=14 Hz), 3.91 (1H, d, J=14 Hz), 4.13 (3H, m), 4.44 (2H, q, J=7 Hz), 6.63 (1H, d, J=8 Hz), 7.14 (1H, d, J=8 Hz), 7.26 (1H, m), 7.28 (1H, t, J=8 Hz), 7.68 (1H, br d, J=8 Hz),8.52 (1H, dd, J1=5 Hz, J2=2 Hz), 8.58 (1H, d, J=2 Hz).

Provenance & Evidence