4-Methylmorpholine → N-(indazol-5-yl) N2-(4-pyridylmethyl)-anthranilic acid amide

HRID 1244293Notes

Reaction equation

HRID 1244293 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH:8][C:9]2[C:10](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:11]([OH:13])=O)=[CH:3][CH:2]=1.[NH2:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][N:23]=[CH:22]2.CN1CCOCC1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[NH:24]1[C:25]2[C:21](=[CH:20][C:19]([NH:18][C:11](=[O:13])[C:10]3[C:9](=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:8][CH2:7][C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)=[CH:27][CH:26]=2)[CH:22]=[N:23]1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 880121H-Indazol-5-amineHCID 516892Sodium BicarbonateHCID 3239010HCID 3239010, compoundHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 69590332N-(indazol-5-yl) N2-(4-pyridylmethyl)-anthranilic acid amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

228 mg of N-(4-pyridylmethyl)-anthranilic acid is introduced into 10 ml of dimethylformamide under argon and in a moisture-free environment. 266 mg of 5-aminoindazole, 0.27 ml of methylmorpholine and 456 mg of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) are added. The mixture is then stirred for 4 hours at room temperature. It is then mixed with dilute sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic phases are washed with water, dried, filtered and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel with ethyl acetate as an eluant.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic phases are washed with water
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation in a vacuum
  6. customThe residue is chromatographed on silica gel with ethyl acetate as an eluant

Sources & evidence

ORD record
ord-e9be399065004956a7937ac19f607d89
Source dataset
uspto-grants-2006_10
Patent number
US07122547B1

Reaction notes

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