HCID 86589866, compound → HCID 69694538, compound

HRID 489912Notes

Reaction equation

HRID 489912 reaction equation
[CH2:1]([N:3]([CH2:34][CH3:35])[C:4]([C:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([C:20]3[C:21]4[C:26]([CH:27]=[C:28]5[C:33]=3[CH:32]=[CH:31][CH:30]=[CH:29]5)=[CH:25][CH:24]=[CH:23][CH:22]=4)=[O:19])[CH2:14][CH2:13]2)[CH:7]=1)=[O:5])[CH3:2]>CO.[Pd]>[CH2:34]([N:3]([CH2:1][CH3:2])[C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH:12]2[CH2:13][CH2:14][N:15]([C:18]([C:20]3[C:33]4[C:28]([CH:27]=[C:26]5[C:21]=3[CH2:22][CH2:23][CH2:24][CH2:25]5)=[CH:29][CH:30]=[CH:31][CH:32]=4)=[O:19])[CH2:16][CH2:17]2)[CH2:7]1)=[O:5])[CH3:35]

Participants

4

Reactant 1

HCID 86589866HCID 86589866, compound

Product 1

HCID 69694538HCID 69694538, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1′-(Anthracene-9-carbonyl)-5,6,1′,2′,3′,4′,5′,6′-octahydro-4H-[1,4′]bipyridinyl-3-carboxylic acid diethylamide (0.033 mmol, 15.5 mg) was dissolved in methanol (˜20 mL), 10% palladium on carbon (10% w/w) (30 mg) was added and the suspension was shaken under a hydrogen atmosphere (45 psi) for 42 h at room temperature in a Parr shaker. The catalyst was filtered off, the solvent evaporated and the residue was purified by chromatography on silica gel eluting with a 1%-5% methanol-dichloromethane gradient to give the title compound (5.3 mg, 34%).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent evaporated
  3. customthe residue was purified by chromatography on silica gel eluting with a 1%-5% methanol-dichloromethane gradient

Sources & evidence

ORD record
ord-ae429facf4a84b499a09a0412fa4b60c
Source dataset
uspto-grants-2005_12
Patent number
US06979741B2

Reaction notes

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