HCID 68951461, compound → HCID 10388152, compound

HRID 751000Notes

Reaction equation

HRID 751000 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:30]=[CH:31][C:32]=2[O:33][CH3:34])[N:10]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[C:20]([C:27]([OH:29])=[O:28])[CH:19]=2)[CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>CCOC(C)=O.CCO.O=[Pt]=O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:30]=[CH:31][C:32]=2[O:33][CH3:34])[N:10]([C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[C:20]([C:27]([OH:29])=[O:28])[CH:19]=2)[CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 68951461HCID 68951461, compound

Product 1

HCID 10388152HCID 10388152, compoundYield 28%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-cyclopentyloxy-4-methoxy-N-(3-carboxy-4-nitrophenyl)-N-(3-pyridylmethyl)aniline (200 mg, 0.43 mmol) in 20 mL of EtOAc and 5 mL of EtOH was hydrogenated at atmospheric pressure over 20 mg of PtO2 with stirring for 16 hours. The catalyst was removed by filtration and the solution concentrated. The residue was chromatographed over SiO2 using MeOH/DCM (1/10) as eluant. The oily residue was further purified by trituration with 1 mL of CH3CN to give 52 mg (28% yield) of the target compound.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe solution concentrated
  3. customThe residue was chromatographed over SiO2
  4. customThe oily residue was further purified by trituration with 1 mL of CH3CN

Sources & evidence

ORD record
ord-dfa6dfb67d9e41fd8196331d2df638bc
Source dataset
uspto-grants-2008_07
Patent number
US07405230B2

Reaction notes

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