Diisopropylethylamine → HCID 58158496, Verbindung

HRID 2095955Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2095955
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]3[N:11]([CH:13]=[C:14]([NH:16][C:17]([CH:19]4[CH2:21][CH2:20]4)=[O:18])[N:15]=3)[CH:12]=2)=[C:4]([F:24])[CH:3]=1.[F:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]2[C:37]([CH3:38])=[CH:36][C:35]([CH3:39])=[C:34]([C:40](O)=[O:41])[C:33]2=[O:43])=[CH:28][CH:27]=1.C(N(CC)C(C)C)(C)C.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)C=O.C(OCC)(=O)C>[CH:19]1([C:17]([NH:16][C:14]2[N:15]=[C:10]3[CH:9]=[CH:8][C:7]([O:6][C:5]4[CH:22]=[CH:23][C:2]([NH:1][C:40]([C:34]5[C:33](=[O:43])[N:32]([C:29]6[CH:28]=[CH:27][C:26]([F:25])=[CH:31][CH:30]=6)[C:37]([CH3:38])=[CH:36][C:35]=5[CH3:39])=[O:41])=[CH:3][C:4]=4[F:24])=[CH:12][N:11]3[CH:13]=2)=[O:18])[CH2:21][CH2:20]1

Komponenten

8

Edukt 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 612407HCID 612407, VerbindungHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58158605N-[6-(4-amino-2-fluorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

Produkt 1

HCID 58158496HCID 58158496, VerbindungAusbeute 54,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of N-[6-(4-amino-2-fluorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (116 mg, 0.357 mmol) and 1-(4-fluorophenyl)-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid (112 mg, 0.429 mmol) in N,N-dimethylformamide (1 mL) were added N,N-diisopropylethylamine (123 μL, 0.714 mmol) and HATU (163 mg, 0.428 mmol), and the mixture was stirred at room temperature for 4 hr. Ethyl acetate and saturated aqueous sodium hydrogen carbonate solution were added to the reaction mixture, and the mixture was extracted 3 times with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate) to give a white solid. The obtained solid was washed with ethyl acetate and collected by filtration to give the title compound (110 mg, 54%) as a white solid.

Aufarbeitung

  1. extractionthe mixture was extracted 3 times with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate)
  7. customto give a white solid
  8. washThe obtained solid was washed with ethyl acetate
  9. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-d6ad905746df436cace53143826349a7
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445509B2

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