HCID 68708632, compound → HCID 58864508, compound

HRID 1177703Notes

Reaction equation

HRID 1177703 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C:4]([NH:17]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]=[CH:9]2>CO.[Pd]>[CH3:1][O:2][C:3](=[O:28])[CH:4]([NH2:17])[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]=[CH:9]2

Participants

4

Reactant 1

HCID 68708632HCID 68708632, compound

Product 1

HCID 58864508HCID 58864508, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-benzyloxycarbonylamino-3-(7-ethyl-1H-indazol-5-yl)-acrylic acid methyl ester (330 mg, 0.78 mmol) in methanol (5 mL) under nitrogen was added palladium on charcoal (10%, 33 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 to give 210 mg (98%) which was used without purification. 1H-NMR (CDCl3, 500 MHz) δ 1.34 (t, J=7.6, 3H), 2.85 (q, J=7.6, 2H), 2.96 (dd, J=13.7, 7.6, 1H), 3.19 (dd, J=13.7, 8.6, 1H), 3.48 (s, 2H), 3.73 (s, 3H), 3.80 (dd, J=7.6, 5.2, 1H), 6.99 (s, 1H), 7.38 (s, 1H), 7.97 (s, 1H). Mass spec.: 248.15 (MH)+.

Workup

  1. customThe flask was flushed with hydrogen
  2. customThe reaction was flushed with nitrogen
  3. filtrationfiltered through celite
  4. concentrationconcentrated
  5. customto give 210 mg (98%) which
  6. customwas used without purification

Sources & evidence

ORD record
ord-a60b3a70ad8047dd950cccd89c6eb167
Source dataset
uspto-grants-2010_11
Patent number
US07842808B2

Reaction notes

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