Pyridine → 2-({[5-(3,5-Difluorophenyl)thiophen-2-yl]sulfonyl}amino)-5-methyl-1,3-thiazole-4-carboxylic acid

Participants

Reaction Steps

A solution of methyl 2-amino-5-methyl-1,3-thiazole-4-carboxylate (25 mg, 0.15 mmol), 5-(3,5-difluorophenyl)thiophene-2-sulfonyl chloride (43 mg, 0.15 mmol) (Intermediate 21) and pyridine (23 mg, 0.29 mmol) in MeCN (1 mL) was stirred at 50° C. for 2 days. After evaporation of the solvents, the residue was dissolved in THF (1 mL) and 2 M LiOH (1 mL) was added. The reaction mixture was stirred at room temperature over night. The reaction mixture was neutralized with 4 M HCl (0.3 mL) and the solvents were removed by evaporation. The crude material was dissolved in MeCN/water (1:1). The product precipitated and the title compound was obtained in 9% yield (5.8 mg). 1H NMR (400 MHz, MeOH-d4) δ ppm 2.56 (s, 3 H) 6.97 (tt, J=9.05, 2.27 Hz, 1 H) 7.26-7.34 (m, 2 H) 7.45 (d, J=3.91 Hz, 1 H) 7.58 (d, J=3.91 Hz, 1 H). MS (ESI+) m/z 417 [M+H]+.

Provenance & Evidence