Triethylamine → HCID 54597253, compound

Participants

Reaction Steps

Et3N (27.56 mg, 37.96 μL, 0.2724 mmol) was added to a stirred solution of 2-ethynyl-6-(4-isopropylsulfonylphenyl)pyrazine (65 mg, 0.2270 mmol) and N-hydroxybenzimidoyl chloride (35.32 mg, 0.2270 mmol) in DMF (2 mL) and the reaction was stirred at ambient temperature for 45 minutes then heated to 65° C. for 1 hour. The mixture was cooled to ambient temperature and diluted with EtOAc and water and the layers separated. The aqueous layer was extracted with EtOAc (×2) and the combined organic extracts washed with water (×3), brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion™, 12 g column, eluting with 0 to 40% EtOAc/Petroleum Ether) and the relevant fractions concentrated in vacuo. The residue was triturated from methanol and the precipitate isolated by filtration to give the title product as a cream solid (30 mg, 33% Yield). 1H NMR (400.0 MHz, DMSO) H NMR (400.0 MHz, DMSO) d 9.53 (s, 1H), 9.32 (s, 1H), 8.58 (d, 2H), 8.09-8.07 (m, 3H), 8.04-8.02 (m, 2H), 7.61-7.57 (m, 3H), 3.55 (sept, 1H) and 1.21 (d, 6H) ppm; MS (ES+) 406.1; LCMS Retention time 1.72 min.

Provenance & Evidence