Dimethylformamide → 2,6-Dichloro-N-{[(1S,3S)-1-hydroxy-3-methylcyclohexyl]methyl}quinoline-5-carboxamide

Participants

Reaction Steps

To a stirred suspension of 2,6-dichloro-quinoline-5-carboxylic acid (2.40 g) (WO2004/106305, Example 76, step b) in dichloromethane (100 ml) was added oxalyl chloride (3.15 g, 2.16 ml) and a drop of N,N-dimethylformamide. The reaction was stirred at room temperature for 2 hours before the volatiles were removed in vacuo and the residue diluted in dichloromethane (100 ml). To this solution were added (1S,3S)-1-(aminomethyl)-3-methylcyclohexanol.HCl (1.78 g) and diisopropylethylamine (6.70 ml) and the reaction stirred for 20 hours before washing with water. The organic layer was dried (MgSO4), filtered and the volatiles were evaporated to provide a crude solid. The material was recrystallised from toluene to provide the subtitle compound as a beige solid (2.5 g).

Provenance & Evidence