Diisopropylethylamine → N-(4-{3-amino-6-[2-(4-morpholinyl)-4-pyridinyl]-2-pyrazinyl}phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

HRID 1853096Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1853096
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]([OH:10])=O)[C:4](=[O:11])[N:3]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=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.[NH2:51][C:52]1[CH:57]=[CH:56][C:55]([C:58]2[C:59]([NH2:76])=[N:60][CH:61]=[C:62]([C:64]3[CH:69]=[CH:68][N:67]=[C:66]([N:70]4[CH2:75][CH2:74][O:73][CH2:72][CH2:71]4)[CH:65]=3)[N:63]=2)=[CH:54][CH:53]=1>C(Cl)Cl.CN(C=O)C.O>[NH2:76][C:59]1[C:58]([C:55]2[CH:56]=[CH:57][C:52]([NH:51][C:8]([C:5]3[C:4](=[O:11])[N:3]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[N:2]([CH3:1])[C:6]=3[CH3:7])=[O:10])=[CH:53][CH:54]=2)=[N:63][C:62]([C:64]2[CH:69]=[CH:68][N:67]=[C:66]([N:70]3[CH2:75][CH2:74][O:73][CH2:72][CH2:71]3)[CH:65]=2)=[CH:61][N:60]=1

Komponenten

8

Edukt 4

HCID 81531DiisopropylethylamineHCID 246564Antipyric acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 682888223-(4-Aminophenyl)-5-[2-(4-morpholinyl)-4-pyridinyl]-2-pyrazinamine

Produkt 1

HCID 68289162N-(4-{3-amino-6-[2-(4-morpholinyl)-4-pyridinyl]-2-pyrazinyl}phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideAusbeute 82,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To the compound prepared in Example 1 (0.100 g) in 5 mL of DCM, 1.0 mL of DMF and N,N-diisopropylethylamine (DIEA) (0.072 g) was added the HATU (0.164 g) and stirred for 30 minutes. To the activated ester was added the compound prepared in Example 13 (0.15 g) and stirred for 1 hour. The reaction mixture was diluted with water, extracted with additional DCM, and the organic layer was washed with water, brine and dried over anhydrous Na2SO4. The DCM layer was filtered and concentrated, and the crude was chromatographed on silica gel using 10:1 DCM:MeOH to give the title compound (0.2 g) having the following physical data.

Aufarbeitung

  1. stirringstirred for 1 hour
  2. extractionextracted with additional DCM
  3. washthe organic layer was washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationThe DCM layer was filtered
  6. concentrationconcentrated
  7. customthe crude was chromatographed on silica gel using 10:1 DCM

Quellen und Nachweise

ORD-Eintrag
ord-335b95ccc5c94fd798393012b9a8b798
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962623B2

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