Diisopropylethylamine → N-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-5-methyl-2-pyridinecarboxamide

HRID 1616038

Reaktionsgleichung

Reaktionsgleichung von HRID 1616038
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH:44]1[C:52]2[C:47](=[C:48]([C:53]3[CH:54]=[C:55]([NH2:62])[C:56]4[CH:57]=[N:58][NH:59][C:60]=4[CH:61]=3)[CH:49]=[CH:50][CH:51]=2)[CH:46]=[CH:45]1>CN(C=O)C.CS(C)=O.CO.CO>[NH:44]1[C:52]2[C:47](=[C:48]([C:53]3[CH:61]=[C:60]4[C:56]([CH:57]=[N:58][NH:59]4)=[C:55]([NH:62][C:8]([C:5]4[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=4)=[O:10])[CH:54]=3)[CH:49]=[CH:50][CH:51]=2)[CH:46]=[CH:45]1

Komponenten

8

Edukt 4

HCID 81531DiisopropylethylamineHCID 1995755-Methylpicolinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 582680196-(1H-indol-4-yl)-1H-indazol-4-amine

Produkt 1

HCID 44539833N-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-5-methyl-2-pyridinecarboxamideAusbeute 27,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 22036561Dimethyl sulfoxide methanolLösungsmittel

Versuchsvorschrift

To a solution of 5-methyl-2-pyridinecarboxylic acid (55 mg, 0.40 mmol, available from Synchem OHG) in DMF (2 ml) was added HATU (150 mg, 0.40 mmol) and DIPEA (0.211 ml, 1.21 mmol). The mixture was stirred at room temperature for 20 mins then 6-(1H-indol-4-yl)-1H-indazol-4-amine (50 mg, 0.20 mmol) was added and the mixture stirred at room temperature for 18 h. The reaction mixture was added to the top of a 2 g aminopropyl cartridge that had been preconditioned with MeOH. The reaction mixture remained on the cartridges for 3 h before being eluted with MeOH. The solvent was removed in vacuo to give a crude residue that was dissolved in DMSO/MeOH (1:1) and purified by Mass Directed Automated Preparative HPLC (Method C). The product was loaded onto a 1 g aminopropyl column, eluted with DCM/MeOH (1:1) and the solvent removed under a stream of nitrogen to give the title compound (20 mg) as a cream solid.

Aufarbeitung

  1. stirringthe mixture stirred at room temperature for 18 h
  2. additionThe reaction mixture was added to the top of a 2 g aminopropyl cartridge that
  3. waitThe reaction mixture remained on the cartridges for 3 h
  4. washbefore being eluted with MeOH
  5. customThe solvent was removed in vacuo
  6. customto give a crude residue that
  7. custompurified by Mass Directed Automated Preparative HPLC (Method C)
  8. washeluted with DCM/MeOH (1:1)
  9. customthe solvent removed under a stream of nitrogen

Quellen und Nachweise

ORD-Eintrag
ord-5f2abde5298c432bb02888b36cf659d2
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765743B2

Verknüpfte Notizen

Wird geladen…