HCID 22064679, compound → HCID 22064672, compound

HRID 1828105Notes

Reaction equation

HRID 1828105 reaction equation
[C:1]([C:3]1[CH:27]=[CH:26][C:6]([CH2:7][NH:8][C:9](=[O:25])[CH:10]([O:22][CH2:23][CH3:24])[N:11]2[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[CH3:20])[C:12]2=[O:21])=[C:5]([N+:28]([O-])=O)[CH:4]=1)#[N:2]>C(OCC)(=O)C.[Pd]>[NH2:28][C:5]1[CH:4]=[C:3]([C:1]#[N:2])[CH:27]=[CH:26][C:6]=1[CH2:7][NH:8][C:9](=[O:25])[CH:10]([O:22][CH2:23][CH3:24])[N:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH3:20])[C:12]1=[O:21]

Participants

4

Reactant 1

HCID 22064679HCID 22064679, compound

Product 1

HCID 22064672HCID 22064672, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (RS)-N-(4-cyano-2-nitro-benzyl)-2-ethoxy-2-(4-methyl-1-oxo-1,3-dihydro-isoindol-2-yl)-acetamide (0.382 g) in ethyl acetate (9 ml) was added 10% Pd/C (190 mg) and the mixture vigorously stirred at r.t. under a hydrogen atmosphere for 16 h. The catalyst was filtered over a celite pad and the cake was carefully washed with ethyl acetate. The filtrate was evaporated to yield (RS)-N-(2-amino-4-cyano-benzyl)-2-ethoxy-2-(4-methyl-1-oxo-1,3-dihydro-isoindol-2-yl)-acetamide (0.354 g) as off-white foam, MS 379.4 ([M+H]+).

Workup

  1. filtrationThe catalyst was filtered over a celite pad
  2. washthe cake was carefully washed with ethyl acetate
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-327e9249b93d499b89b1fa545799d9a6
Source dataset
uspto-grants-2006_06
Patent number
US07056932B2

Reaction notes

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