Trifluoroacetic acid → HCID 59177760, compound

Participants

Reaction Steps

The title compound (73 mg, 66%) was prepared as a white solid from 1,1-dimethylethyl 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate (prepared as in Example 150, Step 2, 0.10 g, 0.22 mmol) and TFA (0.18 mL) in CH2Cl2 (6 mL) then K2CO3 (0.62 g) and 2-chloro-5-(trifluoromethyl)pyridine (50 mg, 0.27 mmol) in DMSO (5 mL) in a manner similar to Example 80. The crude material was purified by chromatography on a silica gel column eluted with 1:16 acetone/CH2Cl2 to give the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.40 (d, 1H, J=2.9 Hz), 8.36 (s, 1H), 8.24 (d, 2H, J=8.3 Hz), 8.02 (d, 1H, J=8.8 Hz), 7.95 (d, 2H, J=8.3 Hz), 7.75-7.70 (m, 1H), 7.51 (dd, 1H, Ja=8.8 Hz, Jb=3.0 Hz), 6.94 (d, 1H, J=9.1 Hz), 4.50-4.40 (m, 2H), 3.99 (d, 2H, J=6.4 Hz), 3.21 (s, 3H), 3.00-2.90 (m, 2H), 2.20-2.05 (m, 1H), 1.90-1.80 (m, 2H), 1.35-1.20 (m, 2H); LRMS (ESI), m/z 492 (M+H).

Provenance & Evidence