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

HRID 2382937Notes

Reaction equation

HRID 2382937 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2089d0fe10ca4293818512857d3d89ce
Source dataset
uspto-grants-2012_09
Patent number
US08263597B2

Reaction notes

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