HCID 66813055, compound → HCID 44515079, compound

HRID 13133Notes

Reaction equation

HRID 13133 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]([O:25][C:26]2[CH:27]=[C:28]3[C:32](=[CH:33][CH:34]=2)[N:31]([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)[N:30]=[CH:29]3)[C@@H:9]([NH:19][C:20](=[O:24])[CH2:21][O:22][CH3:23])[CH2:10][O:11]CC2C=CC=CC=2)[CH:5]=[CH:6][CH:7]=1.[H][H]>C(O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH:8]([O:25][C:26]2[CH:27]=[C:28]3[C:32](=[CH:33][CH:34]=2)[N:31]([C:35]2[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=2)[N:30]=[CH:29]3)[C@@H:9]([NH:19][C:20](=[O:24])[CH2:21][O:22][CH3:23])[CH2:10][OH:11])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 66813055HCID 66813055, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 44515079HCID 44515079, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-[(1S)-2-(3-Fluorophenyl)-2-{[1-(4-fluorophenyl)-1H-indazole-5-yl]oxy}-1-(benzyloxymethyl)ethyl]-2-methoxyacetamide (15 mg, 0.027 mmol) is dissolved in 10 mL ethanol and Pd (10% on charcoal, 0.29 mg, 0.0027 mmol) is added. The reaction mixture is charged with hydrogen and stirred for 2 h at r.t. After filtration of the reaction mixture via a glass microfibre filter, the solvent evaporated and the residue purified by chromatography (silicagel, eluents: ethylacetate/hexane). 7.5 mg (59.6%) of the title compound as a mixture of stereoisomers are obtained.

Workup

  1. filtrationAfter filtration of the reaction mixture via a glass microfibre
  2. filtrationfilter
  3. customthe solvent evaporated
  4. customthe residue purified by chromatography (silicagel, eluents: ethylacetate/hexane)
  5. addition7.5 mg (59.6%) of the title compound as a mixture of stereoisomers
  6. customare obtained

Sources & evidence

ORD record
ord-7f1bc3a91b8749e398437e9654a38820
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Reaction notes

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