1-Methylpiperazine → HCID 73330789, compound

Participants

Reaction Steps

A solution of 5-(2-((2-chloropyridin-4-yl)methyl)-1-methyl-1H-imidazol-4-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole (60 mg, 0.138 mmol) and 1-methylpiperazine (2 mL) in DIPEA (2 mL) was stirred at 150° C. for 5 h. After cooled to RT, the mixture was quenched by water (5 mL), and extracted with EtOAc (2×10 mL). The combined organic phases were washed with water (5 mL) and brine (5 mL), dried (Na2SO4), filtered, and concentrated to afford the crude product, which was purified with prep-HPLC (Mobile phase:A=0.01% formic acid/water, B=acetonitrile; Gradient: B=36%-95% in 18 min; Column: XBridge C18, 5 um, 30 mm×150 mm) to give 5-(1-methyl-2-((2-(4-methylpiperazin-1-yl)pyridin-4-yl)methyl)-1H-imidazol-4-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole as a white solid (8.8 mg, 12.8%). MS (ES+) C24H24F3N7O2 requires: 499, found: 500 [M+H]+; 1H-NMR (500 MHz, CDCl3) δ ppm 8.20 (d, J=7.5 Hz, 2H), 8.14 (d, J=5.0 Hz, 1H), 7.63 (t, 1H), 7.32 (d, J=4 Hz, 2H), 6.58 (d, J=5 Hz, 1H), 6.47 (s, 1H), 4.53 (s, 2H), 3.79-3.74 (m, 2H), 3.63-3.58 (m, 2H), 3.56 (s, 3H), 3.29-3.25 (m, 2H), 2.92-2.87 (m, 2H), 2.79 (s, 3H).

Provenance & Evidence