4-Methylmorpholine → 1-(4-Fluoro-phenyl)-1H-indazole-4-carboxylic acid (1-naphthalen-1-yl-ethyl)-amide

HRID 2382937Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2382937
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([C:17]([OH:19])=O)[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[C:44]1([CH:54]([NH2:56])[CH3:55])[C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH:47]=[CH:46][CH:45]=1.CN1CCOCC1>CC(N(C)C)=O>[C:44]1([CH:54]([NH:56][C:17]([C:12]2[C:11]3[CH:10]=[N:9][N:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[C:16]=3[CH:15]=[CH:14][CH:13]=2)=[O:19])[CH3:55])[C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH:47]=[CH:46][CH:45]=1

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 980891-(1-Naphthyl)ethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 581387741-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid

Produkt 1

HCID 444684381-(4-Fluoro-phenyl)-1H-indazole-4-carboxylic acid (1-naphthalen-1-yl-ethyl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel2×

Versuchsvorschrift

1-(4-Fluoro-phenyl)-1H-indazole-4-carboxylic acid (40.0 mg, 0.156 mmol) and O-(7-azabenzotriazole-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (89 mg, 0.23 mmol) were combined in a 20 mL vial and dimethylacetamide (DMA) (1 mL) was added. The yellow solution was stirred at room temperature for 10 minutes and then a solution of 1-(1-napthyl)ethylamine (40.1 mg, 0.234 mmol) and N-methylmorpholine (NMM) (0.086 mL, 0.78 mmol) in DMA (0.20 mL) was added. The mixture was shaken at room temperature for 16 hours then the solution was evaporated in vacuo. The crude product was purified by preparative reversed-phase HPLC to afford the title compound.

Aufarbeitung

  1. stirringThe mixture was shaken at room temperature for 16 hours
  2. customthe solution was evaporated in vacuo
  3. customThe crude product was purified by preparative reversed-phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-2089d0fe10ca4293818512857d3d89ce
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263597B2

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