Trifluoroacetic acid → 1-Methylethyl 4-[({2-[4-(methylsulfonyl)phenyl]-5-pyrimidinyl}oxy)methyl]-1-piperidinecarboxylate

Participants

Reaction Steps

The title compound (80 mg, 92%) was prepared as a white solid from 1,1-dimethylethyl 4-[({2-[4-(methylsulfonyl)phenyl]-5-pyrimidinyl}oxy)methyl]-1-piperidinecarboxylate (Example 128, 90 mg, 0.20 mmol) and TFA (1.0 mL) in CH2Cl2 (6 mL) then diisopropylethylamine (1.0 ml) and isopropyl chloroformate (1.0M in toluene, 0.22 mL, 0.22 mmol) in a manner similar to Example 74. 1H NMR (400 MHz, CDCl3): δ 8.56 (d, 2H, J=8.5 Hz), 8.48 (s, 2H), 8.02 (d, 2H, J=8.6 Hz), 4.92 (septet, 1H, J=6.2 Hz), 4.24 (bs, 2H), 3.97 (d, 2H, J=6.3 Hz), 3.08 (s, 3H), 2.85-2.70 (m, 2H), 2.10-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.40-1.20 (m, 8H); LRMS (APCI), m/z 434 (M+H).

Provenance & Evidence