Triethylamine → HCID 59700593, compound

Participants

Reaction Steps

Thionyl chloride (2.0 ml) was added to a solution of 2-(N-(4-bromobenzenesulphonyl)-N-methylaminomethyl)thiazole carboxylic acid (460 mg, 1.2 mmol) in dichloromethane (20 ml) and the solution heated at reflux for 2 h. The mixture was cooled to room temperature, reduced in vacuo and azeotroped with toluene to yield a white solid. This was dissolved in dichloromethane (20 ml) and to it were added triethylamine (0.34 ml, 250 mg, 2.4 mmol) and 1,2,3,4-tetrahydroquinoline (0.18 ml, 190 mg, 1.4 mmol). After stirring for 1 h the mixture was reduced in vacuo. Chromatography (50% EtOAc/50% hexanes) afforded 1-(2-(N-(4-bromobenzenesulphonyl)-N-methylaminomethyl)thiazole-4-carbonyl)-1,2,3,4-tetrahydroquinoline (580 mg, 97%) as a white solid.

Provenance & Evidence