Trifluoroacetic acid → HCID 50902337, compound

Participants

Reaction Steps

Trifluoroacetic acid (1 mL) was added to a stirred solution of tert-butyl ((4aS,5S,7aS)-7a-(5-(5-(difluoromethyl)pyrazine-2-carboxamido)-2-fluorophenyl)-3-ethyl-4-oxo-5-(trifluoromethyl)-3,4,4a,5,7,7a-hexahydrofuro[3,4-d]pyrimidin-2-yl)carbamate (115 mg, 0.19 mmol) in DCM (1 mL) at RT. The volatiles were removed in vacuo and the residue was azeotroped with toluene (×1). The free base was isolated by loading this material on to a SCX cartridge (5 g) and eluting with MeOH (2×20 mL) and then 2M NH3 in MeOH (1×20 mL). The ammonia-methanol fraction was evaporated and the residue was treated with Et2O-hexanes to give a solid which was isolated by filtration and dried in vacuo to give the title compound (85 mg, cream solid). 1H NMR (400 MHz, MeOH-d4) δ ppm 1.12 (t, J=7.07 Hz, 3H) 3.65-3.81 (m, 2H) 3.94-4.03 (m, 1H) 4.29-4.35 (m, 1H) 4.36-4.41 (m, 1H) 4.56-4.66 (m, 1H) 6.95 (t, J=55.30 Hz, 1H) 7.19 (dd, J=11.49, 8.97 Hz, 1H) 7.74-7.81 (m, 1H) 7.97 (dd, J=6.95, 2.40 Hz, 1H) 9.02 (s, 1H) 9.40 (s, 1H).

Provenance & Evidence