Cyclopropanecarboxylic acid → HCID 68513327, Verbindung

HRID 1929339Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1929339
F[P-](F)(F)(F)(F)F.CN(C(N(C)C)=[N+]1C2C(=NC=CC=2)[NH+]([O-])N1)C.[CH:25]1([C:28]([OH:30])=O)[CH2:27][CH2:26]1.C(N(C(C)C)CC)(C)C.FC(F)(F)C([O-])=O.[Cl:47][C:48]1[CH:65]=[CH:64][CH:63]=[C:62]([Cl:66])[C:49]=1[CH2:50][O:51][C:52]1[CH:53]=[CH:54][C:55]2[N:59]=[C:58]([NH3+:60])[NH:57][C:56]=2[CH:61]=1>CN(C)C=O>[Cl:47][C:48]1[CH:65]=[CH:64][CH:63]=[C:62]([Cl:66])[C:49]=1[CH2:50][O:51][C:52]1[CH:53]=[CH:54][C:55]2[N:59]=[C:58]([NH:60][C:28]([CH:25]3[CH2:27][CH2:26]3)=[O:30])[NH:57][C:56]=2[CH:61]=1

Komponenten

6

Edukt 4

HCID 15655Cyclopropanecarboxylic acidHCID 81531DiisopropylethylamineHCID 178484287HCID 178484287, VerbindungHCID 178525664HCID 178525664, Verbindung

Produkt 1

HCID 68513327HCID 68513327, VerbindungAusbeute 28,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

a solution of 270 mg of 1-[bis(dimethylamino)methylidene]-2,3-dihydro-1H-[1,2,3]triazolo[4,5-b]pyridin-1-ium-3-oxide hexafluorophosphate, 61 mg of cyclopropanecarboxylic acid and 176 mg of diisopropylethylamine in 40 cm3 of N,N-dimethylformamide is stirred for one hour at a temperature close to 20° C. Then 250 mg of 6-[(2,6-dichlorobenzyl)oxy]-1H-benzimidazol-2-aminium trifluoroacetate is added and the orange solution obtained is stirred for about twenty hours at about 20° C. After concentration under reduced pressure (0.2 kPa), the residue is taken up in 40 cm3 of water and the mixture obtained is extracted three times with 40 cm3 of ethyl acetate. The combined organic phases are washed three times with 40 cm3 of water, then dried over magnesium sulphate, filtered and concentrated under reduced pressure. After purification of the residue by flash chromatography on silica [eluent: dichloromethane/methanol (95/5 by volume)], we obtain 64 mg of N-{6-[(2,6-dichlorobenzyl)oxy]-1H-benzimidazol-2-yl}cyclopropanecarboxamide in the form of a white powder, which has the following characteristics:

Aufarbeitung

  1. customclose to 20° C
  2. customthe orange solution obtained
  3. concentrationAfter concentration under reduced pressure (0.2 kPa)
  4. customthe mixture obtained
  5. extractionis extracted three times with 40 cm3 of ethyl acetate
  6. washThe combined organic phases are washed three times with 40 cm3 of water
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customAfter purification of the residue by flash chromatography on silica [eluent: dichloromethane/methanol (95/5 by volume)], we

Quellen und Nachweise

ORD-Eintrag
ord-0b7b7ba935d4475e885f4c8a0beefbd1
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188078B2

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