HCID 59156764, compound → HCID 44624772, compound

HRID 2390837Notes

Reaction equation

HRID 2390837 reaction equation
[CH3:1][O:2][C:3]1[C:8](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)=[CH:7][C:6]([C:20]2[C:21](=[O:26])[NH:22][CH:23]=[CH:24][CH:25]=2)=[CH:5][C:4]=1[C:27]1([CH3:30])[CH2:29][CH2:28]1>CO.CCOC(C)=O.[Pd]>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:20]3[C:21](=[O:26])[NH:22][CH:23]=[CH:24][CH:25]=3)[CH:5]=[C:4]([C:27]3([CH3:30])[CH2:29][CH2:28]3)[C:3]=2[O:2][CH3:1])=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 59156764HCID 59156764, compound

Product 1

HCID 44624772HCID 44624772, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a suspension of 136 (0.14 g, 0.35 mmol) in MeOH-EtOAc (2:1, 7.5 mL) was added 10% Pd/C (0.014 g), and the reaction mixture was stirred under a hydrogen atmosphere maintained by a balloon for 16 h. The reaction mixture was filtered through diatomaceous earth and the pad was rinsed successively with EtOAc, MeOH and DCM. The combined filtrates were concentrated under reduced pressure, and the crude residue was purified by SiO2 chromatography eluting with EtOAc/hexane to afford 0.095 g (76%) of 3-[3-[2-(4-amino-phenyl)-ethyl]-4-methoxy-5-(1-methylcyclopropyl)phenyl]-1H-pyridin-2-one (I-99) as a light yellow powder.

Workup

  1. temperaturemaintained by a balloon for 16 h
  2. filtrationThe reaction mixture was filtered through diatomaceous earth
  3. washthe pad was rinsed successively with EtOAc, MeOH and DCM
  4. concentrationThe combined filtrates were concentrated under reduced pressure
  5. customthe crude residue was purified by SiO2 chromatography
  6. washeluting with EtOAc/hexane

Sources & evidence

ORD record
ord-19f34f36a90545558a65bf9881f3ea72
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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