4-Pyridinemethanamine → HCID 68768913, compound

Participants

Reaction Steps

To a mixture of racemic-(trans)-2-{4-[(3-phenoxybenzyl)amino]phenyl}cyclopropanecarboxylic acid (I-2a) (0.10 g, 0.231 mmol) in dichloromethane (2 mL) and DMF (3 mL) was added HATU (0.27 g, 0.71 mmol). The mixture was stirred for 15 min followed by addition of 4-(aminomethyl)pyridine (0.10 g, 0.94 mmol). The solution stirred for 6 h after which the dichloromethane was removed via rotavap. Sat. NaHCO3 and ethyl acetate were added and the organic layer separated and washed with H2O, dried over MgSO4, filtered and concentrated. The resulting oil was triterated with Et2O and formed a cream ppt which was filtered and dried under high vacuum to give the title compound as a cream powder (0.08 g, 40%). 1H NMR (400 MHz, CDCl3) δ 8.56 (d, J=5.4 Hz, 2H), 7.34-7.28 (m, 3H), 7.26 (d, J=5.5 Hz, 2H), 7.11-7.07 (m, 2H), 7.01-6.99 (m, 3H), 6.92-6.90 (m, 3H), 6.55 (d, J=8.4 Hz, 2H), 6.01-5.98 (m, 1H), 4.50-4.47 (m, 2H), 4.29 (s, 2H), 4.03 (s, 1H), 2.48-2.43 (m, 1H), 1.58-1.51 (m, 1H), 1.24-1.19 (m, 2H). ES-MS m/z 450 (MH+).

Provenance & Evidence