Triethylamine → (2S)-1-(4-Fluoro-benzenesulfonyl)-pyrrolidine-2-carboxylic acid [4-(4-trifluoromethyl-phenyl)-pyrimidin-2-ylmethyl]-amide

Participants

Reaction Steps

A mixture of C-[4-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-methylamine (92 mg, 0.4 mmol), (S)-1-(4-fluoro-benzenesulfonyl)-pyrrolidine-2-carboxylic acid (99 mg, 0.4 mmol), N-(3-dimethylamniopropyl)-N′-ethylcarbodiimide hydrochloride (139 mg, 0.72 mmol), 1-hydroxybenzotriazole (98 mg, 0.73 mmol), Et3N (0.15 mL, 1.10 mmol), and DMF (2 mL) was stirred at rt for 12 hours. After 12 h, MeOH (0.5 mL) was added to the reaction mixture and resulting solution was purified by preparative reverse-phase HPLC to afford (35 mg, 19%) of a white solid. MS (ESI): mass calcd. for C23H20F4N4O3S, 508.1; m/z found, 509.5 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 8.86 (d, J=5.3, 1H), 8.38 (d, J=8.1, 2H), 8.37-8.33 (m, 1H), 7.99-7.92 (m, 2H), 7.82 (d, J=8.2, 2H), 7.70 (d, J=5.3, 1H), 7.30-7.25 (m, 1H), 4.93-4.76 (m, 2H), 4.31-4.22 (m, 1H), 3.69 (td, J=7.3, 3.7, 1H), 3.25 (td, J=9.8, 6.7, 1H), 2.36-2.29 (m, 1H), 1.97-1.59 (m, 3H).

Provenance & Evidence