Trifluoroacetic acid → 4-(2-Chloro-4-(5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-6-methylphenoxy)butanoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl 4-(2-chloro-4-(5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-6-methylphenoxy)butanoate (90 mg, 170 μmol) in DCM (5 mL) is cooled to 0° C. before TFA (1 mL) is added. The mixture is stirred at 0° C. for 10 min, then at rt for 30 min. The mixture is again cooled to 0° C. before another portion of TFA (1 mL) is added. Stirring is continued at rt for 2 h. The mixture is concentrated and the crude product is purified by prep. HPLC to give the title compound (59 mg) as white solid; LC-MS: tR=1.14 min, [M+H]+=472.29; 1H NMR (CDCl3): δ 8.13 (s br, 1H), 8.02 (d, J=1.4 Hz, 1H), 7.88 (d, J=0.7 Hz, 1H), 7.47 (s, 1H), 7.25 (s, 1H), 4.05 (t, J=5.9 Hz, 2H), 4.00 (s, 3H), 3.17-3.28 (m, 1H), 2.74 (t, J=7.3 Hz, 2H), 2.39 (s, 3H), 2.21 (quint, J=6.5 Hz, 2H), 2.05-2.15 (m, 2H), 1.81-1.95 (m, 4H), 1.68-1.80 (m, 2H).

Provenance & Evidence