Reaktion #680481

Reaktionsgleichung

acetic acid

1-(4-aminophenyl)butan-1-one

3,5-dimethyl-1-phenyl-1H-pyrazole-4-carbaldehyde

→

title compound

1-{4-[(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-ylmethyl)amino]phenyl}butan-1-one

Lösungsmittel

DCM MeOH

DCM MeOH

DMA

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe vial was capped
2. 2
   Temperaturwas then heated
3. 3
   SonstigeAfter completion of the reaction
4. 4
   Einengenthe reaction mixture was concentrated to dryness
5. 5
   workup.DISSOLUTIONThe resulting residue was dissolved in 1:1 DMSO/MeOH
6. 6
   SonstigePurification by reverse phase HPLC (TFA method)

Vorschrift

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.

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