5-methyl-1H-pyrazole-3-carboxylic acid → HCID 44540242, Verbindung

HRID 244717

Reaktionsgleichung

Reaktionsgleichung von HRID 244717
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7]([OH:9])=O)[CH:3]=1.F[P-](F)(F)(F)(F)F.CN(C(ON1C2=NC=CC=C2N=N1)=[N+](C)C)C.[NH:34]1[C:42]2[C:37](=[C:38]([C:43]3[CH:44]=[C:45]([NH2:58])[C:46]4[C:50]([CH:51]=3)=[N:49][N:48](C3CCCCO3)[CH:47]=4)[CH:39]=[CH:40][CH:41]=2)[CH:36]=[CH:35]1>CN(C=O)C.CCN(C(C)C)C(C)C>[NH:34]1[C:42]2[C:37](=[C:38]([C:43]3[CH:51]=[C:50]4[C:46]([CH:47]=[N:48][NH:49]4)=[C:45]([NH:58][C:7]([C:4]4[CH:3]=[C:2]([CH3:1])[NH:6][N:5]=4)=[O:9])[CH:44]=3)[CH:39]=[CH:40][CH:41]=2)[CH:36]=[CH:35]1

Komponenten

6

Edukt 3

HCID 98225-methyl-1H-pyrazole-3-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 582679956-(1H-Indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine

Produkt 1

HCID 44540242HCID 44540242, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel3×HCID 81531DiisopropylethylamineLösungsmittel

Versuchsvorschrift

5-Methyl-1H-pyrazole-3-carboxylic acid (10 mg) in DMF (0.2 ml) was treated with N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethanaminium hexafluorophosphate (27 mg) in DMF (0.2 ml) and DIPEA (0.03 ml). The reaction mixture was shaken for five min prior to treatment with 6-(1H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (20 mg) in DMF (0.2 ml). The reaction mixture was shaken for five min and left to stand at 22° C. for 18 h. The solvent was removed in vacuo and the product re-dissolved in methanol (1 ml) prior to application on to an SCX SPE cartridge (1 g). The product was eluted after 1 h with 2M ammonia in methanol (2×3 ml), the fractions were combined and concentrated under a stream of nitrogen using blow down apparatus. Purification by mass directed preparative HPLC (Method C) afforded the title compound.

Aufarbeitung

  1. stirringThe reaction mixture was shaken for five min
  2. waitleft
  3. waitto stand at 22° C. for 18 h
  4. customThe solvent was removed in vacuo
  5. dissolutionthe product re-dissolved in methanol (1 ml)
  6. washThe product was eluted after 1 h with 2M ammonia in methanol (2×3 ml)
  7. concentrationconcentrated under a stream of nitrogen using blow down apparatus
  8. customPurification by mass

Quellen und Nachweise

ORD-Eintrag
ord-222ac297bb7d4c768557abf89a2cb8ca
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658635B2

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