Diisopropylethylamine → Methyl 4-[1-({[5-chloro-3-(3-chlorobenzyl)-2-thienyl]carbonyl}amino)ethyl]benzoate

Participants

Reaction Conditions

Reaction Steps

The solution containing 5-chloro-3-(3-chlorobenzyl)thiophene-2-carboxylic acid from Example 1, Step 6 (200 mg, 0.696 mmol) and (±)-1-[4-(methoxycarbonyl)phenyl]ethanaminium chloride prepared according to Example 1, Steps 7 to 9 (180 mg, 0.835 mmol) in DMF was cooled to 0° C. and to it was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (317 mg, 0.835 mmol) followed by N,N-diisopropylethylamine (304 μL, 1.74 mmol, 2.5 eq) dropwise. The mixture was stirred at 0° C. for 15 min and diluted with water and EtOAc/ether. The organic layer was washed with water, brine, dried and filtered. The crude was purified by Combi Flash chromatography system (10-40% EtOAc/hexane in 15 min.) to give the desired product as a white solid.

Provenance & Evidence