O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → HCID 52919085, compound

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Reaction Steps

A mixture of TBTU (108 mg, 0.338 mmol), TEA (0.128 mL), 2-chloro-5-(tert-butylcarbonylamino)methyl-benzoic acid (83 mg, 0.31 mmol) and 5 mL THF was stirred for 15 min at rt. Then N-(4-bromophenyl)-2-chloro-5-amino-benzoic acid amide (100 mg, 0.31 mmol, prepared analogously to 2d/2e) was added and it was stirred for 3 h at rt and for additional 3 h at reflux. The mixture was concentrated i.vac., EtOAc was added and the organic phase was washed with 1M NaOH, water, 2M aq. HCl-solution, water and brine and dried with Na2SO4. The crude mixture was concentrated i.vac. and purified by chromatography (silica gel, petrol ether/EtOAc 60/40→55/45) to furnish the title compound.

Provenance & Evidence