Trifluoroacetic acid → HCID 66673149, compound

Participants

Reaction Steps

A mixture of 1,1-dimethylethyl{2-[({4′-[({1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl)oxy]-4-biphenylyl}sulfonyl)amino]ethyl}carbamate (Example 108, 160 mg, 0.27 mmol) and TFA (0.3 mL) in CH2Cl2 (3 mL) was stirred at ambient temperature for 1 h. The crude product was concentrated and purified by reverse-phase preparative HPLC using a CH3CN:H2O gradient (0.5:99.5 to 90:10) with 0.05% TFA as a modifier to give 123 mg (91%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.09 (bs, 2H), 7.86 (d, 2H, J=8.2 Hz), 7.60 (d, 2H, J=8.2 Hz), 7.46 (d, 2H, J=8.8 Hz), 7.33 (bs, 1H), 6.92 (d, 2H, J=8.8 Hz), 4.24-4.14 (m, 2H), 3.84 (d, 2H, J=6.2 Hz), 3.27 (bs, 4H), 3.14-3.04 (m, 2H), 2.94-2.81 (m, 1H), 2.10-2.00 (m, 1H), 1.98-1.88 (m, 2H), 1.51-1.37 (m, 2H), 1.27 (d, 6H, J=7.0 Hz); LRMS (ESI), m/z 500 (M+H).

Provenance & Evidence