Potassium Carbonate → N-[2-({(3R)-1-[1-(4-cyanophenyl)piperidin-4-yl]pyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(2-oxo-2-{[(3R)-1-piperidin-4-ylpyrrolidin-3-yl]amino}ethyl)-3-(trifluoromethyl)benzamide (33 mg, 0.083 mmol) in DMSO (3 mL) was added K2CO3 (17.2 mg, 0.124 mmol) followed by 4-fluorobenzonitrile (10 mg, 0.83 mmol). The mixture was heated to 120° C. for 16 hours. The crude mixture was subjected to column chromatography (15% MeOH, 1% NH4OH in EtOAc) to afford N-[2-({(3R)-1-[1-(4-cyanophenyl)piperidin-4-yl]pyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamide (0.031 g, 75%) as a white solid. 1H-NMR (CDCl3) δ: 1.48-1.70 (m, 3H), 1.82-1.96 (m, 2H), 2.20-2.42 (m, 3H), 2.58-2.76 (m, 2H), 2.84-3.00 (m, 3H), 3.70-3.82 (m, 2H), 4.08 (d, J=4.8 Hz, 2H), 4.38-4.51 (m, 1H), 6.45 (d, J=7.5 Hz, 1H), 6.82 (d, J=9.0 Hz, 2H), 7.18-7.27 (m, 1H), 7.44 (d, J=8.7 Hz, 2H), 7.54 (t, J=7.8 Hz, 1H), 7.74 (d, J=8.7 Hz, 1H), 7.96 (d, J=7.8 Hz, 1H), 8.07 (s, 1H). MS m/z: 500 (M+1).

Provenance & Evidence