Dimethylformamide → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-nitro-1-benzofuran-2-carboxamide

HRID 15462

Reaktionsgleichung

Reaktionsgleichung von HRID 15462
[N+]([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-])=O.Cl.Cl.[NH2:18][C@@H:19]1[CH:24]2[CH2:25][CH2:26][N:21]([CH2:22][CH2:23]2)[CH2:20]1.CN(C([O:34][N:35]1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.CN(C=[O:64])C>>[N:21]12[CH2:26][CH2:25][CH:24]([CH2:23][CH2:22]1)[C@@H:19]([NH:18][C:11]([C:9]1[O:10][C:6]3[C:5]([N+:35]([O-:34])=[O:64])=[CH:4][CH:15]=[CH:14][C:7]=3[CH:8]=1)=[O:13])[CH2:20]2

Komponenten

6

Edukt 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12494972(R)-(+)-3-Aminoquinuclidine DihydrochlorideHCID 131907266-Nitro-1-benzofuran-2-carboxylic acid

Produkt 1

HCID 59341430N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-nitro-1-benzofuran-2-carboxamide

Versuchsvorschrift

1040 mg (5.02 mmol) of 6-nitrobenzofuran-2-carboxylic acid, 1000 mg (5.02 mmol) of (R)-3-aminoquinuclidine dihydrochloride, 2290 mg (6.03 mmol) of HATU, 2250 mg (18.08 mmol) of N,N-diisopropylethylamine and 9 ml of DMF are reacted according to the general procedure (variant B). DMF is removed under reduced pressure. The product is taken up in 100 ml of 1N aqueous sodium hydroxide solution and extracted three times with in each case 50 ml of ethyl acetate. The combined organic phases are washed eight times with 1N aqueous sodium hydroxide solution and once with saturated sodium chloride solution and then dried over magnesium sulfate, and the solvent is removed under reduced pressure using a rotary evaporator. 1.34 g (79% of theory) of the title compound are obtained.

Aufarbeitung

  1. customDMF is removed under reduced pressure
  2. extractionextracted three times with in each case 50 ml of ethyl acetate
  3. washThe combined organic phases are washed eight times with 1N aqueous sodium hydroxide solution
  4. dry with materialonce with saturated sodium chloride solution and then dried over magnesium sulfate
  5. customthe solvent is removed under reduced pressure
  6. customa rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-305ee33818314552b45ed63c07444bb1
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732477B2

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