8-benzyloxy-5-{1-hydroxy-2-[1-(4-methoxy-benzyl)-cyclopropylamino]-ethyl}-1H-quinolin-2-one → 8-hydroxy-5-{1-hydroxy-2-[1-(4-methoxy-benzyl)-cyclopropylamino]-ethyl}-1H-quinolin-2-one

HRID 29852Notes

Reaction equation

HRID 29852 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:20]([OH:35])[CH2:21][NH:22][C:23]2([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[CH2:25][CH2:24]2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH:20]([OH:35])[CH2:21][NH:22][C:23]2([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=3)[CH2:24][CH2:25]2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2

Participants

4

Reactant 1

HCID 231060808-benzyloxy-5-{1-hydroxy-2-[1-(4-methoxy-benzyl)-cyclopropylamino]-ethyl}-1H-quinolin-2-one

Product 1

HCID 115017828-hydroxy-5-{1-hydroxy-2-[1-(4-methoxy-benzyl)-cyclopropylamino]-ethyl}-1H-quinolin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

258 mg (0.51 mmol) 8-benzyloxy-5-{1-hydroxy-2-[1-(4-methoxy-benzyl)-cyclopropylamino]-ethyl}-1H-quinolin-2-one in 10 mL methanol are hydrogenated with palladium on charcoal as catalyst at 3 bar. Then the catalyst is separated off, the solvent is distilled off and the residue is purified by chromatography (reverse phase, water/acetonitrile gradient). Yield: 12 mg (6%); mass spectroscopy: [M+H]+=381.

Workup

  1. customThen the catalyst is separated off
  2. distillationthe solvent is distilled off
  3. customthe residue is purified by chromatography (reverse phase, water/acetonitrile gradient)

Sources & evidence

ORD record
ord-595e29f16dd2436bb391b71713daa4be
Source dataset
uspto-grants-2008_09
Patent number
US07423035B2

Reaction notes

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