HCID 178436419, compound → HCID 178436420, compound

HRID 2355960Notes

Reaction equation

HRID 2355960 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C:4]([NH:18]C(OCC1C=CC=CC=1)=O)=[CH:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([CH2:15][CH3:16])[CH:14]=1)[NH:11][N:10]=[C:9]2[CH3:17]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:29])[CH:4]([NH2:18])[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([CH2:15][CH3:16])[CH:14]=1)[NH:11][N:10]=[C:9]2[CH3:17]

Participants

4

Reactant 1

HCID 178436419HCID 178436419, compound

Product 1

HCID 178436420HCID 178436420, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Benzyloxycarbonylamino-3-(7-ethyl-3-methyl-1H-indazol-5-yl)-acrylic acid methyl ester (1.0 g, 2.54 mmol) in methanol (15 mL) was flushed with nitrogen, and treated with palladium on charcoal (10%, 100 mg). The flask was flushed with hydrogen and allowed to stir under an atmosphere of hydrogen overnight. The reaction was flushed with nitrogen, filtered through celite, and concentrated. Column chromatography gave 0.6 g (91%) of the desired material. 1H-NMR (CD3OD) δ 1.32 (m, 3H), 2.50 (s, 3H), 2.88 (dd, J=7.3, 7.6, 1H), 2.89 (dd, J=7.6, 7.6, 1H), 3.02 (dd, J=6.4, 7.0, 1H), 3.11 (dd, J=7.6, 5.8, 1H), 3.35 (s, 1H), 3.65 (m, 3H), 7.00 (s, 1H), 7.33 (s, 1H). Mass spec.: 262.24 (MH)+.

Workup

  1. customThe flask was flushed with hydrogen
  2. customThe reaction was flushed with nitrogen
  3. filtrationfiltered through celite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-41f4bb8e69314ae89297c69eb2d52e80
Source dataset
uspto-grants-2010_07
Patent number
US07754732B2

Reaction notes

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