Triethylamine → 4-(3-chloro-4-(N-(4-chlorobenzenesulphonyl)-N-methylaminomethyl)thiophene-2-carbonyl)-N-(3-methyl-1,2,4-oxadiazol-5-ylmethyl)benzomorpholine-2-carboxamide

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Reaction Steps

A solution of 3-chloro-4-(N-(4-chlorobenzenesulphonyl)-N-methylaminomethyl)-thiophene-2-carboxylic acid (57 mg, 0.15 mmol) in thionyl chloride (2 ml) and dichloromethane (5 ml) was heated at reflux for 1 h. The mixture was cooled and reduced in vacuo. The residue was added to a solution of N-(3-methyl-1,2,4-oxadiazol-5-ylmethyl)benzomorpholine-2-carboxamide (40 mg, 0.15 mmol) and triethylamine (42 μl, 0.30 mmol) in dichloromethane (10 ml) and stirred at room temperature for 3 days. The mixture was reduced and chromatography (30% EtOAc/70% hexanes and 100% EtOAc) afforded 4-(3-chloro-4-(N-(4-chlorobenzenesulphonyl)-N-methylaminomethyl)thiophene-2-carbonyl)-N-(3-methyl-1,2,4-oxadiazol-5-ylmethyl)benzomorpholine-2-carboxamide as a colourless oil (31 mg, 33%).

Provenance & Evidence