4-Methylmorpholine → N-(6-chloroindazol-5-yl)-2-[(4-pyridyl)methyl]amino-benzoic acid amide

HRID 1793457Notes

Reaction equation

HRID 1793457 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=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][C:27]=1[Cl:28])[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>CN(C)C=O.O>[Cl:28][C:27]1[CH:26]=[C:25]2[C:21]([CH:22]=[N:23][NH:24]2)=[CH:20][C:19]=1[NH:18][C:11](=[O:13])[C:10]1[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=1[NH:8][CH2:7][C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 3239010HCID 3239010, compoundHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 220224116-Chloro-1H-indazol-5-amine

Product 1

HCID 10199623N-(6-chloroindazol-5-yl)-2-[(4-pyridyl)methyl]amino-benzoic acid amideYield 30.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

194 mg (0.85 mmol) of 2-(4-pyridylmethyl)aminobenzoic acid is mixed in 8 ml of dimethylformamide with 283 mg (1.69 mmol) of 5-amino-6-chloroindazole. Under argon and in a moisture-free environment, 215 mg (2.13 mmol) of N-methylmorpholine and 386 mg (1.02 mmol) of O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophophate are added to this solution. This mixture is stirred for 4 hours at room temperature. It is then diluted with about 40 ml of water and extracted three times with 30 ml of ethyl acetate each. The combined organic phase is washed with water, dried, filtered and concentrated by evaporation. The residue is chromatographed on silica gel with methylene chloride:ethanol-10:1 as an eluant. 97 mg (30.2% of theory) of N-(6-chloroindazol-5-yl)-2-[(4-pyridyl)methyl]amino-benzoic acid amide with a melting point of 222.8° C. is obtained.

Workup

  1. extractionextracted three times with 30 ml of ethyl acetate each
  2. washThe combined organic phase is washed with water
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation
  6. customThe residue is chromatographed on silica gel with methylene chloride

Sources & evidence

ORD record
ord-8deb4794e9dc40f1ab3e81c5e63b38a3
Source dataset
uspto-grants-2006_07
Patent number
US07081468B2

Reaction notes

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