HCID 67486653, compound → HCID 67486162, compound

HRID 2371274Notes

Reaction equation

HRID 2371274 reaction equation
[O:1]1[C:6]2=[CH:7][CH:8]=[CH:9][C:5]2=[CH:4][CH:3]=[C:2]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17](=[O:39])[CH:18]([C:29]1[CH:34]=[CH:33][C:32]([C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:31][CH:30]=1)[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=1>O1CCCC1.[OH-].[OH-].[Pd+2]>[NH2:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][CH:18]([C:29]2[CH:30]=[CH:31][C:32]([C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:33][CH:34]=2)[C:17]([NH:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:2]2[O:1][C:6]3=[CH:7][CH:8]=[CH:9][C:5]3=[CH:4][CH:3]=2)=[O:39])=[CH:21][CH:22]=1

Participants

4

Reactant 1

HCID 67486653HCID 67486653, compound

Product 1

HCID 67486162HCID 67486162, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To N-(4-Benzofuran-2-yl-phenyl)-2-(4-tert-butyl-phenyl)-3-(4-nitro-phenyl)-propionamide (830 mg, 1.6 mmol) in tetrahydrofuran (20 ml) was added 20% palladium hydroxide on carbon (172 mg). The reaction mixture was stirred under hydrogen for 16 h, filtered and concentrated. Chromatography of the residue (20% ethyl acetate in hexane) afforded 3-(4-Amino-phenyl)-N-(4-benzofuran-2-yl-phenyl)-2-(4-tert-butyl-phenyl)-propionamide as a white solid (600 mg, 77%).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-59bd5363bde646f39ba564aa579df31c
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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