Isopropylamine → tert-Butyl 3-(4-(5-(5-chloro-6-isopropylaminopyridin-3-yl)-1,2,4-oxadiazol-3-yl)-3-methylphenyl)propanoate

Participants

Reaction Steps

A solution of 31 mg (0.07 mmol) of tert-butyl 3-(4-(5-(5,6-dichloropyridin-3-yl)-1,2,4-oxadiazol-3-yl)-3-methylphenyl)propanoate (from EXAMPLE 15, Step A) and 120 μL (1.4 mmol) of 2-propylamine in 5.0 mL of THF was heated to 100° C. in a sealed tube overnight. The mixture was cooled to rt and concentrated. Chromatography on a Biotage 40S cartridge using 1:9 v/v Et2O/hexanes as the eluant gave 28 mg of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.32 (d, J=6.4, 6H), 1.43 (s, 9H), 2.57 (t, J=7.7, 2H), 2.64 (s, 3H), 2.94 (t, J=7.7, 2H), 4.41 (m, 1H), 5.32 (d, J=7.5, 1H), 7.16-7.17 (m, 2H), 7.99 (d, J=8.5, 1H), 8.18 (d, J=1.8, 1H), 8.85 (d, J=1.8, 1H).

Provenance & Evidence