Pyridine → HCID 86689196, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 2-amino-4-methylthiazole-5-carboxylate (9.3 mg, 0.050 mmol), 5-chloro-3-methyl-benzothiophene-2-sulfonyl chloride (14 mg, 0.050 mmol) and pyridine (8 μL, 0.100 mmol) in MeCN (400 μL) was heated at 60° C. for 7 days. The solvent was removed and the residue redissolved in 1 M NaOH (300 μL, 0.300 mmol) and then heated at 60° C. over night. The crude product was diluted with water/MeOH/DMSO and acidified by addition of TFA. The product was purified by reversed phase chromatography (ACE C8, 5 μm, 21×50 mm, flow 25 ml/min, gradient: 0.1% TFA in water/MeCN over 6 minutes). The title compound was obtained in 24% yield (4.9 mg). 1H NMR (500 MHz, MeOH-d4) δ ppm 2.47 (s, 3 H) 2.65 (s, 3H) 7.47 (dd, J=8.67, 2.08 Hz, 1 H) 7.88 (dd, J=8.67, 0.51 Hz, 1 H) 7.89 (dd, J=2.08, 0.51 Hz, 1 H). MS (ESI+) m/z 403 [M+H]+.

Provenance & Evidence