Trifluoroacetic acid → 4-Oxo-3-azabicyclo[3.1.0]hexane-1-carboxylic acid [1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-yl]amide

Reaktionsgleichung

[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][CH3:20])[CH:13]=3)=[CH:10][C:9]([NH:21][C:22]([C:24]34[CH2:29][CH:28]3[C:27](=[O:30])[N:26](CC3C=CC(OC)=CC=3OC)[CH2:25]4)=[O:23])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>>[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][CH3:20])[CH:13]=3)=[CH:10][C:9]([NH:21][C:22]([C:24]34[CH2:29][CH:28]3[C:27](=[O:30])[NH:26][CH2:25]4)=[O:23])=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

Edukt 3

HCID 6422Trifluoroacetic acid

HCID 7519Anisole

HCID 894658043-(2,4-Dimethoxybenzyl)-4-oxo-3-azabicyclo[3.1.0]hexane-1-carboxylic acid [1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-yl]amide

Produkt 1

HCID 712878104-Oxo-3-azabicyclo[3.1.0]hexane-1-carboxylic acid [1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-yl]amideAusbeute 6,5 %

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To 3-(2,4-dimethoxybenzyl)-4-oxo-3-azabicyclo[3.1.0]hexane-1-carboxylic acid[1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-yl]amide (6.3 mg) were sequentially added anisole (2 μl) and trifluoroacetic acid (0.5 ml) at room temperature, and the mixture was stirred at 80° C. for 3 hours. This reaction mixture was concentrated under reduced pressure, the resulting residue was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=9/1) to give the titled compound (0.3 mg).

Aufarbeitung

customat room temperature
concentrationThis reaction mixture was concentrated under reduced pressure
customthe resulting residue was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=9/1)

Quellen und Nachweise

ORD-Eintrag: ord-b1516c525a35452c827a7c5a61ad8e36
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08846746B2

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