Trifluoroacetic acid → HCID 54597088, compound

Participants

Reaction Steps

TFA (200 μL, 2.596 mmol) was added to a stirred solution of tert-butyl 1-(3-amino-6-(4-(isopropylsulfonyl)phenyl)pyrazin-2-yl)pyrrolidin-3-ylcarbamate (46 mg, 0.09966 mmol) in DCM (5 mL) at ambient temperature. The reaction was stirred at this temperature for 17 hours. A further portion of TFA (200 μL, 2.596 mmol) was added and the reaction stirred at ambient temperature for a further 2 hours. The solvent was removed in vacuo and the residue was azeotroped with DCM/ether (×3). The residue was passed through a 2 g SCX-2 cartridge and washed with MeOH. The product was eluted by washing the cartridge with 2M NH3 in MeOH. The residue was purified by column chromatography (ISCO Companion™, 12 g column, elueting with 0 to 10% MeOH+10% NH4OH/DCM) to give the title product as a yellow solid (17.2 mg, 45% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.17 (d, 6H), 1.61-1.70 (m, 1H), 1.97-2.06 (m, 1H), 3.01 (br s, 2H), 3.22 (dd, 1H), 3.38 (quin, 1H), 3.48-3.57 (m, 2H), 3.65-3.74 (m, 2H), 6.12 (br s, 2H), 7.84 (d, 2H), 8.13 (s, 1H) and 8.17 (d, 2H) ppm; (ES+) 362.3.

Provenance & Evidence