HCID 69459677, compound → HCID 69459918, compound

HRID 969465Notes

Reaction equation

HRID 969465 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:20]([OH:35])[CH2:21][NH:22][C:23]([CH3:34])([CH3:33])[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[F:32])=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)C1C=CC=CC=1>CO.[Pd]>[F:32][C:26]1[CH:27]=[C:28]([F:31])[CH:29]=[CH:30][C:25]=1[CH2:24][C:23]([NH:22][CH2:21][CH:20]([C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[C:18]2[C:13]=1[CH2:14][CH2:15][C:16](=[O:19])[NH:17]2)[OH:35])([CH3:33])[CH3:34]

Participants

4

Reactant 1

HCID 69459677HCID 69459677, compound

Product 1

HCID 69459918HCID 69459918, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 220 mg (0.5 mmol) 8-benzyloxy-5-{2-[2-(2,4-difluoro-phenyl)-1,1-dimethyl-ethylamino]-1-hydroxy-ethyl}-1H-quinolin-2-one in 10 mL methanol is hydrogenated in the presence of palladium on charcoal at ambient temperature and normal pressure. Then the catalyst is separated off, the filtrate is evaporated down and the residue is chromatographed (reverse phase; water/acetonitrile gradient).

Workup

  1. customThen the catalyst is separated off
  2. customthe filtrate is evaporated down
  3. customthe residue is chromatographed (reverse phase; water/acetonitrile gradient)

Sources & evidence

ORD record
ord-eefb1c3489244838afd841f0be854723
Source dataset
uspto-grants-2007_12
Patent number
US07307076B2

Reaction notes

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