1-Hydroxybenzotriazole → HCID 71510275, Verbindung

HRID 83492Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 83492
[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.[CH3:24][C@H:25]1[C:29](=[O:30])[NH:28][CH2:27][C@@H:26]1[C:31](O)=[O:32].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>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:31]([C@@H:26]3[C@@H:25]([CH3:24])[C:29](=[O:30])[NH:28][CH2:27]3)=[O:32])=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

7

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 712877301-Phenyl-5-(3-(trifluoromethoxy)phenyl)-1H-pyrazol-3-ylamineHCID 86680348(3R,4R)-4-Methyl-5-oxopyrrolidine-3-carboxylic Acid

Produkt 1

HCID 71510275HCID 71510275, VerbindungAusbeute 57,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1-phenyl-5-(3-(trifluoromethoxy)phenyl)-1H-pyrazol-3-ylamine (79 mg) in N,N-dimethylformamide (0.8 ml) were sequentially added (3R,4R)-4-methyl-5-oxopyrrolidine-3-carboxylic acid (46 mg) prepared in Preparation 1, HOBt.H2O (57 mg) and WSC.HCl (71 mg), and the mixture was stirred at room temperature for 2 hours. To this reaction solution were added water and a saturated aqueous solution of sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The separated organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=10/1) to give the titled compound (63 mg).

Aufarbeitung

  1. extractiona saturated aqueous solution of sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate
  2. washThe separated organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-059f61f92b154ebd94a1d7041508eeb3
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846746B2

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