HCID 15549023, compound → HCID 9890668, compound

HRID 1596179Notes

Reaction equation

HRID 1596179 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10]2[CH:15]=[C:14]([C:16]3[N:17]([CH3:44])[C:18]([CH2:31][CH2:32][NH:33]C(OCC4C=CC=CC=4)=O)=[N:19][C:20]=3[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C.[Pd]>[C:1]1([C@@H:7]([NH:9][C:10]2[CH:15]=[C:14]([C:16]3[N:17]([CH3:44])[C:18]([CH2:31][CH2:32][NH2:33])=[N:19][C:20]=3[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 15549023HCID 15549023, compound

Product 1

HCID 9890668HCID 9890668, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (S)-1-phenyl-N-{4-[2-(2-(benzyloxycarbonyl-amino)-ethyl)-3-methyl-5-(3-trifluoromethyl-phenyl)-3H-imidazol-4-yl]-pyridin-2-yl}-ethylamine (0.20 g, 0.33 mmol) in absolute ethanol (10 mL) was flushed with argon before 10% palladium on activated carbon (0.07 g) was added. This reaction mixture, flushed with hydrogen gas, was vigorously stirred under one atmosphere of hydrogen for 5 hrs, then filtered and concentrated. The residue was purified by silica gel chromatography to yield 146 mg of the desired product as an oil.

Workup

  1. additionwas added
  2. customThis reaction mixture, flushed with hydrogen gas
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ff52b4207ca04c058724b78ba7826dde
Source dataset
uspto-grants-2001_09
Patent number
US06291457B1

Reaction notes

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