Pyridine → HCID 178511072, compound

Participants

Reaction Steps

Trifluoroacetic anhydride 0.042 mL, 0.05 mmol) was added to a stirred solution of N-{4-[trans-4-(2-amino-2-oxoethyl)cyclohexyl]phenyl}-5-[(2-fluorophenyl)amino]-1,3,4-oxadiazole-2-carboxamide (Example 516) (20 mg, 0.05 mmol) and pyridine (90 uL, 0.11 mmol) in DCM (2 mL). After 15 minutes DCM (10 mL) was added and the reaction mixture was washed sequentially with 1M HCl (5 mL), water (10 mL) and 10% ammonium hydroxide solution (5 mL) then dried and concentrated under reduced pressure to give the title compound (18 mg, 95%) as a solid; 1H NMR δ 1.13-1.30 (m, 3H), 1.40-1.54 (m, 2H), 1.60-1.75 (m, 1H), 1.76-1.92 (m, 5H), 2.40-2.50 (m, 1H), 7.10-7.19 (m, 1H), 7.20-7.35 (m, 4H), 7.68 (d, 2H), 8.03 (t, 1H), 10.75 (s, 1H), 10.93 (s, 1H); MS m/e MH+ 420.

Provenance & Evidence