Triethylamine → HCID 86620399, compound

Participants

Reaction Conditions

Reaction Steps

4-Chlorobenzylamine (0.17 mL) and triethylamine (0.12 mL) were added in turn to a stirred slurry of 5-(2-acetamido-4-methyl-1,3-thiazol-5-yl)-2-chloropyridine-3-sulfonyl chloride (250 mg) in THF (20 mL) that had been cooled to 0° C. The resultant mixture was stirred at 0° C. for 30 minutes and at room temperature for 1 hour. The mixture was evaporated and the residue was partitioned between dichloromethane and water. The organic solution was washed with a saturated aqueous sodium chloride solution, filtered, dried over magnesium sulfate and evaporated. The material so obtained was purified by ‘basic reversed-phase chromatography’ (Waters ‘Xterra’ C18 reversed-phase silica, 150×21 mm, solvent gradient of 5-50% acetonitrile in water (containing 1% aqueous ammonium hydroxide (d=0.88) solution). The material so obtained was triturated under diethyl ether, isolated and dried at 55° C. under vacuum. There was thus obtained the title compound as a white solid (155 mg); 1H NMR Spectrum: (DMSOd6) 2.22 (s, 3H), 2.40 (s, 3H), 4.24 (s, 2H), 7.25 (s, 4H), 8.06 (m, 1H), 8.63 (m, 1H), 9.06 (br s, 1H), 12.54 (br s, 11H); Mass Spectrum: M+H+ 471 and 473.

Provenance & Evidence