4-Methylmorpholine → HCID 57012812, compound

HRID 1244294Notes

Reaction equation

HRID 1244294 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]([NH2:11])=[CH:4][CH:3]=1.CN1CCOCC1.[NH2:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][N:24]=[CH:23]2.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>O.CN(C)C=O>[NH:25]1[C:26]2[C:22](=[CH:21][C:20]([NH:19][C:7](=[O:9])[C:6]3[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=3)[NH2:11])=[CH:28][CH:27]=2)[CH:23]=[N:24]1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 124762-Amino-5-chlorobenzoic acidHCID 880121H-Indazol-5-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 57012812HCID 57012812, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

171 mg of 5-chloroanthranilic acid is introduced into 10 ml of dimethylformamide under argon and in a moisture-free environment and mixed in succession with 253 mg of N-methylmorpholine, 266 mg of 5-aminoindazole and 456 mg of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) and stirred for 4 hours at room temperature. After standing overnight, it is mixed with 50 ml of water and extracted with 30 ml of ethyl acetate. The organic phase is washed with water, dried, filtered and concentrated by evaporation. The residue is chromatographed on silica gel with ethyl acetate as an eluant. 266 mg of N-(indazol-5-yl)-5-chloroanthranilic acid amide is obtained.

Workup

  1. waitAfter standing overnight
  2. extractionextracted with 30 ml of ethyl acetate
  3. washThe organic phase is washed with water
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customThe residue is chromatographed on silica gel with ethyl acetate as an eluant

Sources & evidence

ORD record
ord-e2e72daa507749b4b972d1d249f320e6
Source dataset
uspto-grants-2006_10
Patent number
US07122547B1

Reaction notes

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