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Diisopropylethylamine → (R)-2-Oxoimidazolidine-4-carboxylic acid[5-(3-butylphenyl)-1-phenyl-1H-pyrazol-3-yl]amide

HRID 83565
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 83565
[CH2:1]([C:5]1[CH:6]=[C:7]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:14]=[C:13]([NH2:22])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4].[O:23]=[C:24]1[NH:28][C@@H:27]([C:29](O)=[O:30])[CH2:26][NH:25]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C)C=O.O>[CH2:1]([C:5]1[CH:6]=[C:7]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:14]=[C:13]([NH:22][C:29]([C@H:27]3[CH2:26][NH:25][C:24](=[O:23])[NH:28]3)=[O:30])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]
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Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 7003745(4R)-2-oxoimidazolidine-4-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866803825-(3-Butylphenyl)-1-phenyl-1H-pyrazol-3-ylamine

Produkt 1

HCID 71287781
(R)-2-Oxoimidazolidine-4-carboxylic acid[5-(3-butylphenyl)-1-phenyl-1H-pyrazol-3-yl]amide
Ausbeute 21,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5-(3-butylphenyl)-1-phenyl-1H-pyrazol-3-ylamine (40 mg) in N,N-dimethylformamide (0.4 ml) were sequentially added (R)-2-oxoimidazolidine-4-carboxylic acid (21 mg) prepared by the same procedures as Preparation 20, HATU (63 mg), diisopropylethylamine (29 μL) at room temperature, and the mixture was stirred for 2 hours. To this reaction mixture was added water, and the mixture was extracted with ethyl acetate. The resulting 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. The resulting residue was purified by silica gel thin-layer chromatography (eluent: n-hexane/acetone=1/5). To the resulting solid was added diisopropyl ether, and the mixture was stirred. A solid was collected from this suspension by filtration, and was dried under reduced pressure to give the titled compound (12 mg).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe resulting organic layer was washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel thin-layer chromatography (eluent: n-hexane/acetone=1/5)
  6. additionTo the resulting solid was added diisopropyl ether
  7. stirringthe mixture was stirred
  8. filtrationA solid was collected from this suspension by filtration
  9. customwas dried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c729d6718d8f41089a0dba673ac2657e
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08846746B2

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