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

HRID 593299

Reaktionsgleichung

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[CH2:9][CH2:10][CH3:11])=[CH:4][CH:3]=1.[CH3:13][C:14]1[C:18]([CH:19]=O)=[C:17]([CH3:21])[N:16]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:15]=1.C(O)(=O)C>C(Cl)Cl.CO.CC(N(C)C)=O>[CH3:13][C:14]1[C:18]([CH2:19][NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8](=[O:12])[CH2:9][CH2:10][CH3:11])=[CH:6][CH:7]=2)=[C:17]([CH3:21])[N:16]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:15]=1

Komponenten

Reaktionsbedingungen

Temperatur: 55 °C

Versuchsvorschrift

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.

Aufarbeitung

customThe vial was capped
temperaturewas then heated
customAfter completion of the reaction
concentrationthe reaction mixture was concentrated to dryness
dissolutionThe resulting residue was dissolved in 1:1 DMSO/MeOH
customPurification by reverse phase HPLC (TFA method)

Quellen und Nachweise

ORD-Eintrag: ord-753f62ebc22d4739aff3da88b7d0bec7
Quelldatensatz: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09242933B2

Verknüpfte Notizen

Wird geladen…