HCID 86748959, compound → HCID 19387379, compound

HRID 2399291Notes

Reaction equation

HRID 2399291 reaction equation
C(O)(C1C=CC=CC=1)C1C=CC=CC=1.[F:15][C:16]([F:57])([F:56])[C:17]1[CH:18]=[C:19]([NH:27][C:28](=[O:55])[NH:29][C:30]2[CH:50]=[C:49]([C:51]([F:54])([F:53])[F:52])[CH:48]=[CH:47][C:31]=2[O:32][C:33]2[CH:41]=[CH:40][C:39]([C:42]([CH3:46])([CH3:45])[CH2:43][CH3:44])=[CH:38][C:34]=2[C:35]([O-:37])=[O:36])[CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1>C(OCC)(=O)C.[Pd]>[F:15][C:16]([F:56])([F:57])[C:17]1[CH:18]=[C:19]([NH:27][C:28](=[O:55])[NH:29][C:30]2[CH:50]=[C:49]([C:51]([F:54])([F:53])[F:52])[CH:48]=[CH:47][C:31]=2[O:32][C:33]2[CH:41]=[CH:40][C:39]([C:42]([CH3:45])([CH3:46])[CH2:43][CH3:44])=[CH:38][C:34]=2[C:35]([OH:37])=[O:36])[CH:20]=[C:21]([C:23]([F:24])([F:25])[F:26])[CH:22]=1

Participants

4

Reactant 1

HCID 86748959HCID 86748959, compound

Product 1

HCID 19387379HCID 19387379, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Benzhydrol-2-[2-[3-[3,5-bis(trifluoromethyl)phenyl]ureido]-4trifluoromethylphenoxy]-5-(1,1-dimethylpropyl)benzoate (110 mg, 0.0002 mol) was dissolved in ethyl acetate and a palladium on carbon catalyst (50 mg) was added, under argon. The mixture was hydrogenated in a parr bottle at 54 psi, for 16 h. The mixture was filtered through Celite® and washed with ethyl acetate and methanol. The solvents were evaporated and the residue was flash chromatographed (silica gel, ethyl acetate/hexane/formic acid) to yield the title compound; mp 238°-240° C.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. washwashed with ethyl acetate and methanol
  3. customThe solvents were evaporated
  4. customchromatographed (silica gel, ethyl acetate/hexane/formic acid)

Sources & evidence

ORD record
ord-5523cd24ec934c87bb4eddd6a549bed3
Source dataset
uspto-grants-1995_09
Patent number
US05447957

Reaction notes

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