Triethylamine → HCID 45381814, compound

Participants

Reaction Steps

To a solution of 2-amino-4-fluoromethyl-5-(2-isopropyl-2H-pyrazol-3-yl)-benzoic acid methyl ester (243 mg, 0.834 mmol) in DCM (15 mL) were added Et3N (0.35 mL, 3 equiv) and then (CCl3O)2CO (177 mg, 0.7 equiv). The resulting mixture was stirred at r.t. for 1 h. The solvent was removed in vacuo and the crude solubilised in THF. CH3SO2NHNH2 (101 mg, 1.1 equiv) was added and the mixture was stirred at r.t. for 1 h. Then, aq NaOH (1N, 0.92 mL) was added and the mixture was stirred for 30 min. The solvent was removed in vacuo and water was added. The pH was adjusted to 3-4 by addition of 1N aq HCl. The aqueous phase was extracted with AcOEt twice. The organic phases were combined, washed with brine, dried (Na2SO4) and concentrated in vacuo to afford a crude solid. This solid was dissolved into 10 mL of DCM and then 10 ml of hexanes was added. The mixture was sonicated for 1 min. The resulting solid was filtered off, washed with hexanes and high-vacuum dried to afford the title compound (227 mg, 69%) as an off-white solid. (ES-MS: m/z 396.4 [M+H]+, rt 4.39 min) 1H-NMR (DMSO-d6, 400 MHz) 11.07 (bs, 1H); 7.76 (d, 1H, J=1.07 Hz); 7.55 (d, 1H, J=1.58 Hz); 7.40 (s, 1H); 6.30 (d, 1H, J=1.77 Hz); 5.30 (d, 2H, J=46.55 Hz); 4.14 (m, 1H); 3.16 (s, 1H); 1.31 (d, 6H, J=6.51 Hz).

Provenance & Evidence