1-Hydroxybenzotriazole → (R)-5-Oxopyrrolidine-3-carboxylic acid [1-phenyl-5-(3-trifluoromethoxyphenyl)-1H-pyrazol-3-yl]amide

HRID 83506Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 83506
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=3)=[CH:10][C:9]([NH2:23])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:24]=[C:25]1[NH:29][CH2:28][C@H:27]([C:30](O)=[O:31])[CH2:26]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.C(=O)([O-])O.[Na+]>CN(C)C=O.O>[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:20])[F:21])[CH:13]=3)=[CH:10][C:9]([NH:23][C:30]([C@@H:27]3[CH2:26][C:25](=[O:24])[NH:29][CH2:28]3)=[O:31])=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

8

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 28063204(3R)-5-oxopyrrolidine-3-carboxylic acidHCID 712877301-Phenyl-5-(3-(trifluoromethoxy)phenyl)-1H-pyrazol-3-ylamine

Produkt 1

HCID 89465736(R)-5-Oxopyrrolidine-3-carboxylic acid [1-phenyl-5-(3-trifluoromethoxyphenyl)-1H-pyrazol-3-yl]amideAusbeute 83,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1-phenyl-5-(3-(trifluoromethoxy)phenyl)-1H-pyrazol-3-ylamine (40 mg) prepared according to the same procedures as Preparation 2 in N,N-dimethylformamide (0.3 ml) were sequentially added (R)-5-oxopyrrolidine-3-carboxylic acid (24 mg) prepared in Preparation 5, HOBt.H2O (29 mg) and WSC.HCl (36 mg), and the mixture was stirred at room temperature overnight. To this reaction solution were added a saturated aqueous solution of sodium hydrogen carbonate and water, and the mixture was stirred. The insoluble substance was collected by filtration, washed with water, and dried under reduced pressure to give the titled compound (45 mg).

Aufarbeitung

  1. filtrationThe insoluble substance was collected by filtration
  2. washwashed with water
  3. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f66e1398412346f0853f70e6f1cedcf1
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846746B2

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