Acetic Acid → 1-(4-(((3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)methyl)amino)phenyl)butan-1-one

Participants

Reaction Conditions

Reaction Steps

In a 20 ml vial, to a solution of solution of 1-(4-aminophenyl)butan-1-one (46 mg, 0.28 mmol) dissolved in DCM/MeOH (0.6 mL) was added a solution of 3,5-dimethyl-1-phenyl-1H-pyrazole-4-carbaldehyde (112 mg, 0.56 mmol) in DMA (1.8 mL). A solution of acetic acid (50 mg, 0.84 mmol) in DCM/MeOH (0.6 mL) was then added, followed by the addition of 361 mg of MP-CNBH3 resin (3 eq.; subst. 2.34 mmoles/g). The vial was capped and was then heated with shaking overnight at 55° C. The progress of the reaction was monitored by LC/MS. After completion of the reaction, the reaction mixture was concentrated to dryness. The resulting residue was dissolved in 1:1 DMSO/MeOH. Purification by reverse phase HPLC (TFA method) gave the title compound.

Provenance & Evidence