HCID 54673560, compound → HCID 66607003, compound

HRID 563631Notes

Reaction equation

HRID 563631 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:36])[N:10]([CH2:13][C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:15]=1[C:24]1[C:29]([O:30][CH3:31])=[CH:28][CH:27]=[C:26]([CH2:32][C:33]([OH:35])=[O:34])[CH:25]=1)[CH2:11][CH3:12]>CCO.[Pd]>[CH2:11]([N:10]([CH2:13][C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:15]=1[C:24]1[C:29]([O:30][CH3:31])=[CH:28][CH:27]=[C:26]([CH2:32][C:33]([OH:35])=[O:34])[CH:25]=1)[C:9]([NH:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1)=[O:36])[CH3:12]

Participants

4

Reactant 1

HCID 54673560HCID 54673560, compound

Product 1

HCID 66607003HCID 66607003, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of {2′-[3-(2-bromo-phenyl)-1-ethyl-ureidomethyl]-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl}-acetic acid (0.072 g, 0.13 mmol) in EtOH was added 10% palladium on carbon (0.020 g), and the reaction was stirred under H2 using a Parr apparatus overnight. The mixture was filtered through a pad of Celite and concentrated, and the residue was acidified with 1N aqueous HCl and extracted with CH2Cl2. The combined organic layers were dried and concentrated, and the crude material was purified by silica gel chromatography (20-60% EtOAc in hexanes) to give the title compound. M+H is 487.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationconcentrated
  3. extractionextracted with CH2Cl2
  4. customThe combined organic layers were dried
  5. concentrationconcentrated
  6. customthe crude material was purified by silica gel chromatography (20-60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d2065fd3e4b54170afa8cd83ad71c1f2
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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