2-Fluoro-N-methylaniline → 3-(4-Tert-butyl-benzenesulfonylamino)-5-chloro-pyridine-2-carboxylic acid (2-fluoro-phenyl)-methyl-amide

Participants

Reaction Conditions

Reaction Steps

3-(4-tert-Butyl-benzenesulfonylamino)-5-chloro-pyridine-2-carboxylic acid (75 mg, 0.20 mmol), (2-fluoro-phenyl)-methyl-amine (23 mg, 0.61 mmol), HATU (193 mg, 0.51 mmol), TEA (114 μL, 0.81 mmol) and 0.5 mL NMP were combined in a 4 mL vial and stirred overnight at 60° C. HPLC purification (10 to 95% gradient of MeCN-water) provided 3-(4-tert-butyl-benzenesulfonylamino)-5-chloro-pyridine-2-carboxylic acid (2-fluoro-phenyl)-methyl-amide: 1H NMR (400 MHz, CDCl3) 9.98 (s, 1 H), 8.01 (s, 1 H), 7.82 (d, 2H), 7.63 (s, 1 H), 7.51 (d, 2H), 7.13 (m, 1 H), 6.92 (t, 1 H), 6.84 (t, 1 H), 6.37 (m, 1 H), 3.38 (t, 3H), 1.26 (s, 9H); MS m/z 476.1.

Provenance & Evidence