Sodium Bicarbonate → 3-oxa-6-azabicyclo[3.1.1]hept-6-yl(8-(1H-1,2,4-triazol-1-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl)methanone

HRID 931048Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 931048
[N:1]1([C:6]2[C:7]3[N:8]([C:16]([C:19]([OH:21])=O)=[CH:17][N:18]=3)[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=2)[CH:5]=[N:4][CH:3]=[N:2]1.FC(F)(F)C(O)=O.[CH:29]12[CH2:35][CH:33]([NH:34]1)[CH2:32][O:31][CH2:30]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(N(CC)CC)C>[CH:33]12[CH2:35][CH:29]([N:34]1[C:19]([C:16]1[N:8]3[CH:9]=[C:10]([C:12]([F:14])([F:13])[F:15])[CH:11]=[C:6]([N:1]4[CH:5]=[N:4][CH:3]=[N:2]4)[C:7]3=[N:18][CH:17]=1)=[O:21])[CH2:30][O:31][CH2:32]2

Komponenten

7

Edukt 4

HCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118378892HCID 118378892, VerbindungHCID 118378980HCID 118378980, Verbindung

Produkt 1

HCID 1183789023-oxa-6-azabicyclo[3.1.1]hept-6-yl(8-(1H-1,2,4-triazol-1-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl)methanoneAusbeute 57,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 8-(1H-1,2,4-triazol-1-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acid (80 mg), 3-oxa-6-azabicyclo[3.1.1]heptane 2,2,2-trifluoroacetate (75 mg), HATU (133 mg), triethylamine (150 μL) and anhydrous DMF (3 mL) was stirred at room temperature for 12 hr, saturated aqueous sodium bicarbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane), and the obtained solid was recrystallized from ethyl acetate/hexane to give the title compound (59 mg).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  5. customthe obtained solid was recrystallized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-26c40103094144b6bb5719446119ebfc
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296746B2

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