Diisopropylethylamine → 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

HRID 83579

Reaktionsgleichung

Reaktionsgleichung von HRID 83579
[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]([NH2:21])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:22][O:23][C:24]1[CH:40]=[C:39]([O:41][CH3:42])[CH:38]=[CH:37][C:25]=1[CH2:26][N:27]1[C:32](=[O:33])[CH:31]2[C:29]([C:34](O)=[O:35])([CH2:30]2)[CH2:28]1.CCN=C=NCCCN(C)C.Cl.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)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:34]([C:29]34[CH2:30][CH:31]3[C:32](=[O:33])[N:27]([CH2:26][C:25]3[CH:37]=[CH:38][C:39]([O:41][CH3:42])=[CH:40][C:24]=3[O:23][CH3:22])[CH2:28]4)=[O:35])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

8

Edukt 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 712877391-Phenyl-5-(3-propylphenyl)-1H-pyrazol-3-ylamineHCID 866803903-(2,4-Dimethoxybenzyl)-4-oxo-3-azabicyclo[3.1.0]hexane-1-carboxylic Acid

Produkt 1

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]amideAusbeute 90,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-ylamine (3.5 mg) prepared according to the same procedures as Preparation 2-2 in N,N-dimethylformamide (0.5 ml) were sequentially added 3-(2,4-dimethoxybenzyl)-4-oxo-3-azabicyclo[3.1.0]hexane-1-carboxylic acid (3.7 mg) and WSC.HCl (3.6 mg) at room temperature, and the mixture was stirred for 14 hours. To this reaction mixture were added diisopropylethylamine (3.3 μl) and HATU (7.3 mg), and the mixture was stirred at room temperature for additional 72 hours. To this reaction mixture was added water, and the mixture was extracted with ethyl acetate. This organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to give the titled compound (6.3 mg).

Aufarbeitung

  1. customat room temperature
  2. stirringthe mixture was stirred at room temperature for additional 72 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThis organic layer was washed with water
  5. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fde5c8cad4dc4fafaf89f6e45aa25fc3
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846746B2

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