Trifluoroacetic acid → HCID 58864314, compound

HRID 2355867Notes

Reaction equation

HRID 2355867 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4]([NH:16]C(OCC1C=CC=CC=1)=O)=[CH:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([Cl:15])[CH:14]=1)[NH:11][N:10]=[CH:9]2.FC(F)(F)C(O)=O>CO>[CH3:1][O:2][C:3](=[O:27])[CH:4]([NH2:16])[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([Cl:15])[CH:14]=1)[NH:11][N:10]=[CH:9]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68707452Methyl 3-(7-chloro-1H-indazol-5-yl)-2-[[(phenylmethoxy)carbonyl]amino]-2-propenoate

Product 1

HCID 58864314HCID 58864314, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-benzyloxycarbonylamino-3-(7-chloro-1H-indazol-5-yl)-acrylic acid methyl ester (300 mg, 0.78 mmol) in methanol (10 mL) was treated with trifluoroacetic acid (0.2 mL), flushed with nitrogen, and treated with 10% palladium on charcoal (30 mg). The flask was flushed with hydrogen and allowed to stir under an atmosphere of hydrogen. After 4 days, all starting material had been consumed. The reaction was flushed with nitrogen, filtered through celite, and concentrated. Column chromatography gave 78 mg (40%).

Workup

  1. customflushed with nitrogen
  2. additiontreated with 10% palladium on charcoal (30 mg)
  3. customThe flask was flushed with hydrogen
  4. customall starting material had been consumed
  5. customThe reaction was flushed with nitrogen
  6. filtrationfiltered through celite
  7. concentrationconcentrated
  8. customColumn chromatography gave 78 mg (40%)

Sources & evidence

ORD record
ord-becd1b9766f84808aa42109449afefe0
Source dataset
uspto-grants-2010_07
Patent number
US07754732B2

Reaction notes

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