Diisopropylethylamine → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-6-nitro-1-benzofuran-2-carboxamide

HRID 1621030

Reaktionsgleichung

Reaktionsgleichung von HRID 1621030
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]2[CH:8]=[C:9]([C:11]([OH:13])=O)[O:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].CN(C(ON1N=[N:31][C:26]2[CH:27]=[CH:28][CH:29]=[N:30][C:25]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:40](N(CC)C(C)C)(C)[CH3:41]>CN(C=O)C>[N:30]12[CH2:29][CH2:28][CH:27]([CH2:40][CH2:41]1)[C@@H:26]([NH:31][C:11]([C:9]1[O:10][C:6]3[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:15]=[CH:14][C:7]=3[CH:8]=1)=[O:13])[CH2:25]2

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 131907266-Nitro-1-benzofuran-2-carboxylic acid

Produkt 1

HCID 59341358N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-6-nitro-1-benzofuran-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1.3 g (5.02 mmol) of 6-nitro-1-benzofuran-2-carboxylic acid, 1.0 g (5.02 mmol) of R-aminoquinuclidine dihydrochloride, 2.29 g (6.02 mmol) of HATU, 2.34 g (18.07 mmol) of N,N-diisopropylethylamine and 10 ml of DMF are reacted by general method B. The mixture is concentrated in vacuo and extracted with 1 N sodium hydroxide solution and with ethyl acetate, the organic phase is dried over sodium sulfate and concentrated, and the residue is dissolved in methanol. Dowex 50WX2-200 ion exchanger resin is added, and within 1 h, the mixture is concentrated in a rotary evaporator. The resin is washed successively with methanol, DMF, methanol, THF, methanol, dichloromethane, methanol and 10% triethylamine in methanol. The product fraction is concentrated. 1.75 g (99% of theory) of the title compound are obtained.

Aufarbeitung

  1. concentrationThe mixture is concentrated in vacuo
  2. extractionextracted with 1 N sodium hydroxide solution and with ethyl acetate
  3. dry with materialthe organic phase is dried over sodium sulfate
  4. concentrationconcentrated
  5. dissolutionthe residue is dissolved in methanol
  6. additionDowex 50WX2-200 ion exchanger resin is added
  7. concentrationthe mixture is concentrated in a rotary evaporator
  8. washThe resin is washed successively with methanol, DMF, methanol, THF, methanol, dichloromethane, methanol and 10% triethylamine in methanol
  9. concentrationThe product fraction is concentrated

Quellen und Nachweise

ORD-Eintrag
ord-2bca9c911fc84fb8afaa3ce304bc7ec1
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772511B2

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