Acefylline → HCID 45254481, Verbindung

HRID 44428

Reaktionsgleichung

Reaktionsgleichung von HRID 44428
[N:1]1([C:12](=[O:13])[C:11]2[N:10]([CH2:14][C:15]([OH:17])=O)[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]([OH:52])([CH3:51])[CH3:50])=[CH:45][CH:44]=1>CN(C=O)C.CS(C)=O>[CH3:2][N:1]1[C:12](=[O:13])[C:11]2[N:10]([CH2:14][C:15]([NH:42][C:43]3[CH:44]=[CH:45][C:46]([C:49]([OH:52])([CH3:50])[CH3:51])=[CH:47][CH:48]=3)=[O:17])[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4]

Komponenten

5

Edukt 3

HCID 69550AcefyllineHCID 95432612-(4-Aminophenyl)propan-2-olHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 45254481HCID 45254481, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3013483N,N-dimethylformamide; methylsulfinylmethaneLösungsmittel

Versuchsvorschrift

To a 0° C. solution of acid 101 (0.32 g, 1.34 mmol) in DMF/DMSO (1:1, 20 mL) was added HATU (0.0.76 g, 2.01 mmol). The reaction was then stirred an additional 15 min at room temperature. The solution was cooled to 0° C. and amine 135 (0.30 g, 2.01 mmol) was added. The reaction was then stirred at rt overnight. The DMF was concentrated in vacuo and water was added to the reaction. The aqueous layer was extracted with EtOAc The ethyl acetate layer was then washed again with water and the organic layer was concentrated in vacuo. The product was purified by flash chromatography on silica gel eluting with EtOAc/hexanes and EtOAc/MeOH to yield 402 as a pure light brown semi solid (0.086 g, 17.5%). MS (APCI): m/z 372.2 [M−H]+ Anal. Calcd. For C18H21N5O4. 0.35 EtOAc: C, 57.93; H, 5.96; N, 17.41. Found C, 58.36; H, 6.14; N, 16.96.

Aufarbeitung

  1. temperatureThe solution was cooled to 0° C.
  2. stirringThe reaction was then stirred at rt overnight
  3. concentrationThe DMF was concentrated in vacuo and water
  4. additionwas added to the reaction
  5. extractionThe aqueous layer was extracted with EtOAc The ethyl acetate layer
  6. washwas then washed again with water
  7. concentrationthe organic layer was concentrated in vacuo
  8. customThe product was purified by flash chromatography on silica gel eluting with EtOAc/hexanes and EtOAc/MeOH

Quellen und Nachweise

ORD-Eintrag
ord-baba062cb47f4c34aaf02c30011c1cd1
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541423B2

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