Diisopropylethylamine → HCID 58575577, Verbindung

HRID 1807872Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1807872
[CH:1]1([C:4]2[CH:13]=[C:12]3[C:7]([NH:8][C:9](=[O:23])[C:10]4[N:11]3[C:14]([CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[N:15][N:16]=4)=[CH:6][C:5]=2[C:24]([OH:26])=O)[CH2:3][CH2:2]1.BrC1C=C2C(NC(=O)C3N2C(C2CCOCC2)=NN=3)=CC=1C(O)=O.[CH2:51]1[C:59]2[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=2)[CH2:53][NH:52]1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH:1]1([C:4]2[CH:13]=[C:12]3[C:7]([NH:8][C:9](=[O:23])[C:10]4[N:11]3[C:14]([CH:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)=[N:15][N:16]=4)=[CH:6][C:5]=2[C:24]([N:52]2[CH2:53][C:54]3[C:59](=[CH:58][CH:57]=[CH:56][CH:55]=3)[CH2:51]2)=[O:26])[CH2:2][CH2:3]1

Komponenten

8

Edukt 6

HCID 81531DiisopropylethylamineHCID 422478IsoindolineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58575207HCID 58575207, VerbindungHCID 67133878HCID 67133878, Verbindung

Produkt 1

HCID 58575577HCID 58575577, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixed liquid of 95.0 mg of a mixture of 8-cyclopropyl-4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxylic acid and 8-bromo-4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxylic acid, 39.0 mg of isoindoline, 190 μL of diisopropylethylamine, and 1.50 mL of N,N-dimethylformamide was added 156 mg of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate, followed by stirring at room temperature overnight. To the reaction liquid was added a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with chloroform. The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by preparative HPLC (methanol/0.1% aqueous formic acid solution) to obtain 24.8 mg of 8-cyclopropyl-7-(1,3-dihydro-2H-isoindol-2-ylcarbonyl)-1-(tetrahydro-2H-pyran-4-yl)[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one as a pale brown solid.

Aufarbeitung

  1. customTo the reaction liquid
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by preparative HPLC (methanol/0.1% aqueous formic acid solution)

Quellen und Nachweise

ORD-Eintrag
ord-85972d80f0e944ce889a6f722d58a9c7
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08357688B2

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