Trifluoroacetic acid → HCID 58095014, compound

Participants

Reaction Steps

A mixture of 7-[5-(1-allyl-1H-imidazol-2-yl)-4-(2,4-dichlorophenyl)-2-thienyl]-N-(tert-butyl)[1,3]thiazolo[5,4-d]pyrimidin-2-amine (480 mg, 0.886 mmol), trifluoroacetic Acid (2.0 mL) and DCM (6.0 mL) was stirred at rt. After being stirred for 30 min, trifluoromethanesulfonic acid (0.118 mL, 1.33 mmol) was added to the mixture. The mixture was stirred at rt for 49 hours and then the solvent was removed in vacuo. To the residue, sat. NaHCO3 and EtOAc were added. After being stirred for 30 min, the organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was crystallized from EtOAc and Hexane to yield the title compound (352.9 mg, 82%) as a pale yellow solid. LCMS: (AA) ES+ 485, 487. NMR (400 MHz, d6-DMSO) δ: 8.66 (s, 1H), 8.55 (s, 1H), 8.43 (bs, 2H), 7.74 (d, J=2.0 Hz, 1H), 7.41 (dd, J=8.3, 2.3 Hz, 1H), 7.23-7.20 (m, 2H), 7.02 (d, J=1.3 Hz, 1H), 5.68-5.59 (m, 1H), 5.08-5.05 (m, 1H), 4.85-4.80 (m, 1H), 4.35 (d, J=5.5 Hz, 2H).

Provenance & Evidence