Propylamine → HCID 22612364, compound

Participants

Reaction Steps

To a solution of 2-(pyridin-3-yloxy)-nicotinic acid (0.100 g 0.462 mmole), BOP (0.205 grams, 0.463 mmole) and DIEA (0.242 μl) in dimethylformamide (5 ml) was added n-propyl amine (40 μl, 0.486 mmole) and stirred for 4 hours at room temperature. The reaction was quenched with 10 μl water and extracted with ethyl acetate. The combined organics were washed with alternating portions of 5% citric acid and sat'd bicarb, dried over Na2SO4, filtered and concentrated to a product which was purified by chromatography on silica gel eluting with diethyl ether to give a white crystalline solid (0.068 g). M.P. 55-56° C.; 1H H NMR (400 mhz, CDCl3) d 0.98 (t, J=7.3 Hz, 3H), 1.61-1.70 (m, 2H), 3.45-3.50 (m, 2H), 7.19 (dd, J=7.5 Hz, 4.8 Hz, 1H), 7.38-7.41 (m, 1H), 7.52-7.55 (m, 1H), 7.72 (bs, 1H), 8.16 (dd, J=4.8 hz, 2.1 Hz, 1H), 8.52-8.63 (m, 3H).

Provenance & Evidence