HCID 59643238, compound → HCID 59643282, compound

HRID 2251541Notes

Reaction equation

HRID 2251541 reaction equation
[CH3:1][C:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][N:18]([C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-])=O)=[CH:32][N:31]=2)[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)=[CH:12][CH:11]=1)([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4]>CO.[Pd]>[NH2:36][C:33]1[CH:34]=[CH:35][C:30]([N:18]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]([F:29])([F:27])[F:28])=[CH:24][CH:25]=2)[CH2:17][CH2:16][C:13]2[CH:14]=[CH:15][C:10]([O:9][C:2]([CH3:1])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:11][CH:12]=2)=[N:31][CH:32]=1

Participants

4

Reactant 1

HCID 59643238HCID 59643238, compound

Product 1

HCID 59643282HCID 59643282, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of ethyl 2-methyl-2-[4-(2-{(5-nitropyridin-2-yl)[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]propanoate (149 mg; 1.73 mmol) in 10 ml of MeOH was treated with 10% Pd/C (60 mg) and hydrogenated under balloon pressure for 2 hr. The catalyst was filtered off and washed with chloroform/methanol. The filtrate was concentrated and the residue purified by radial chromatography using a methanol-dichloromethane gradient (1–10%) to afford the title compound as a dark-colored oil (125 mg; 89% yield).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with chloroform/methanol
  3. concentrationThe filtrate was concentrated
  4. customthe residue purified by radial chromatography

Sources & evidence

ORD record
ord-39470f786dac4047a402260a107b5c3d
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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