4-Methylmorpholine → HCID 15551933, compound

HRID 1743737Notes

Reaction equation

HRID 1743737 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=O)[CH2:3][CH2:2]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>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[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[NH:8][CH2:7][CH:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)=[CH:27][CH:26]=2)[CH:22]=[N:23]1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 880121H-Indazol-5-amineHCID 22236512HCID 22236512, compound

Product 1

HCID 15551933HCID 15551933, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

235 mg (1 mmol) of 2-(tetrahydropyran-4-yl)methylaminobenzoic acid is mixed in 10 ml of dimethylformamide with 266 mg (2 mmol) of 5-aminoindazole. 253 mg (2.5 mmol) of N-methylmorpholine and 456 mg (1.2 mmol) of O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetamethyluronium hexafluorophosphate are added to this solution under argon and in a moisture-free environment. This mixture is stirred for 3 hours at room temperature. It is concentrated by evaporation in a vacuum, taken up in dilute sodium bicarbonate solution 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 absorptively precipitated in ethyl acetate and suctioned off. The filtrate is concentrated by evaporation, and the residue is chromatographed on silica gel with methylene chloride:ethanol=10:1 as an eluant. 124 mg (35% of theory) of N-(indazol-5-yl)-2-(tetrahydropyran-4-yl)methylaminobenzoic acid amide with a melting point of 173.6° C. is obtained.

Workup

  1. concentrationIt is concentrated by evaporation in a vacuum
  2. extractionextracted three times with 30 ml of ethyl acetate each
  3. washThe combined organic phase is washed with water
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customThe residue is absorptively precipitated in ethyl acetate
  8. concentrationThe filtrate is concentrated by evaporation
  9. customthe residue is chromatographed on silica gel with methylene chloride

Sources & evidence

ORD record
ord-b6c851113df24004a76029dc539bcdb8
Source dataset
uspto-grants-2006_03
Patent number
US07012081B2

Reaction notes

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