Acetic Acid → HCID 178508488, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(8-fluoro-2-phenyl-quinolin-7-yl)-3-methylsulfanyl-imidazo[1,5-a]pyrazin-8-ylamine (24 mg, 0.000060 mol) in AcOH (1 mL, 0.02 mol) was charged with hydrogen bromide (300 uL, 0.006 mol) and refluxed at 118° C. over weekend. An additional 5 eq of HBr were added and the reaction mixture was heated at 118° C. for 4-5 h. The reaction was stopped and cooled in ice. Orange precipitate formed on cooling in ice. The reaction mixture was concentrated in vacuo and washed with hexanes to obtain the title compound as an orange gummy solid. 1H NMR (400 MHz, CD3OD d4): δ=7.56 (dd, J=7.33, 3.28 Hz, 1H), 7.63-7.68 (m, 4H), 7.84-7.90 (m, 1H), 8.15 (d, J=8.84 Hz, 1H), 8.19-8.25 (m, 2H), 8.37 (d, J=8.59 Hz, 1H), 8.87 (d, J=8.84 Hz, 1H). MS (ES+): m/z 388.21 (100). HPLC: tR=2.42 min (Open Lynx polar—5 min). Note: Precipitate formed on cooling in ice. At rt the compound is oily.

Provenance & Evidence