Trifluoroacetic acid → 1-(4-(5-(6-(4-(isopropylsulfonyl)phenyl)pyrazin-2-yl)isoxazol-3-yl)phenyl)-N-methylmethanamine

Participants

Reaction Steps

TFA (500 μL, 6.490 mmol) was added to a stirred solution of tert-butyl N-[[4-[5-[6-(4-isopropylsulfonylphenyl)pyrazin-2-yl]isoxazol-3-yl]phenyl]methyl]-N-methyl-carbamate (85 mg, 0.1549 mmol) in DCM (5 mL) and the reaction was stirred at ambient temperature for 15 hours. The solvent was removed in vacuo and the residue azeotroped with DCM (×2) and ether (×2). The reaction mixture was passed through a 2 g SCX-2 cartridge and washed with MeOH/DCM mixtures. The product was eluted by washing the cartridge with 2M NH3 in MeOH/DCM mixtures. The filtrate was concentrated in vacuo to give the title compound as a yellow solid (45.6 mg, 66% Yield). 1H NMR (400.0 MHz, DMSO) d H NMR (400.0 MHz, DMSO) δ 9.67 (s, 1H), 9.46 (s, 1H), 8.72 (d, 2H), 8.21 (d, 2H), 8.19 (s, 1H), 8.11 (d, 2H), 7.67 (d, 2H), 3.87 (s, 2H), 3.69 (sept, 1H), 2.43 (s, 3H) and 1.35 (d, 6H) ppm; MS (ES+) 449.2; LCMS Retention time: 1.09 min.

Provenance & Evidence