Sulfuric Acid → HCID 178461691, compound

Participants

Reaction Steps

To a cooled solution of 4-[(1R)-1-{4-[(4-(trifluoromethyl)-1,3-thiazol-2-yl)amino]phenyl}ethyl]-1,2,5-oxadiazol-3-amine (0.2 g, 0.56 mmol) in AcOH (5 ml) and 37% HCl (3 ml), a solution of sodium nitrite (44 mg, 0.845 mmol) in water (3 ml) was added dropwise. The resulting reaction mixture was stirred for 30 min, then conc. H2SO4 (0.5 ml) was added and the reaction quenched with a saturated solution of NH4Cl (10 ml); the resulting mixture was extracted with Et2O (3×10 ml) and the collected organic extracts were evaporated under vacuum; the crude was purified by flash chromatography to afford pure 4-[(1R)-1-(4-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)ethyl]-1,2,5-oxadiazol-3-ol (13) (0.17 g, 0.48 mmol) as a white solid (85%). [α]D=−51 (c=1; CH3OH); 1H-NMR (DMSO-d6): δ 8.25 (bs, 1H, NH), 7.40 (d, 2H, J=7 Hz), 7.25 (d, 2H, J=7 Hz), 7.05 (s, 1H), 3.90 (q, 1H, J=7 Hz), 1.75 (d, 3H, J=7 Hz).

Provenance & Evidence