Dimethylformamide → 1-(8-Fluoro-2-phenyl-quinolin-7-yl)-3-(5-methanesulfonylmethylthiazol-2-ylsulfanyl)-imidazo[1,5-a]pyrazin-8-ylamine

Participants

Reaction Conditions

Reaction Steps

A 10 mL microwave vessel was charged with a solution of 8-amino-1-(8-fluoro-2-phenyl-quinolin-7-yl)-2H-imidazo[1,5-a]pyrazine-3-thione (24 mg, 0.000062 mol), 2-chloro-5-[(methylsulfonyl)methyl]-1,3-thiazole (0.026 g, 0.00012 mol), potassium carbonate in DMF (1.7 mL, 0.022 mol). The reaction mixture was heated in the microwave at 100° C. for 10 min. The reaction mixture was heated again at 120° C. for 10 min in the microwave to get full consumption of SM. Reaction mixture was purified by Gilson HPLC eluting with 10→65% acetonitrile: H2O to afford the title compound as an off white solid. 1H NMR (400 MHz, CDCl3): δ=2.85 (s, 3H), 4.36 (s, 2H), 7.34 (d, J=4.80 Hz, 1H), 7.48-7.59 (m, 4H), 7.67 (s, 1H), 7.74-7.78 (m, 2H), 8.04 (d, J=8.84 Hz, 1H), 8.24 (dd, J=8.21, 1.39 Hz, 2H), 8.31 (dd, J=8.72, 1.39 Hz, 1H). MS (ES+): m/z 563.18 (100) [MH+]. HPLC: tR=2.89 min (Open Lynx polar—5 min).

Provenance & Evidence