4-(2-tert-butyl-5-nitro-1H-pyrrole-4-carbonyl)-3,3-dimethylpiperazin-2-one → 4-(2-amino-5-tert-butyl-1H-pyrrole-3-carbonyl)-3,3-dimethylpiperazin-2-one

HRID 18937Notes

Reaction equation

HRID 18937 reaction equation
[C:1]([C:5]1[NH:6][C:7]([N+:21]([O-])=O)=[C:8]([C:10]([N:12]2[CH2:17][CH2:16][NH:15][C:14](=[O:18])[C:13]2([CH3:20])[CH3:19])=[O:11])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:21][C:7]1[NH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:9][C:8]=1[C:10]([N:12]1[CH2:17][CH2:16][NH:15][C:14](=[O:18])[C:13]1([CH3:19])[CH3:20])=[O:11]

Participants

4

Reactant 1

HCID 586793674-(2-tert-butyl-5-nitro-1H-pyrrole-4-carbonyl)-3,3-dimethylpiperazin-2-one

Product 1

HCID 586792354-(2-amino-5-tert-butyl-1H-pyrrole-3-carbonyl)-3,3-dimethylpiperazin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 4-(2-tert-butyl-5-nitro-1H-pyrrole-4-carbonyl)-3,3-dimethylpiperazin-2-one (120 mg) in methanol (10 mL) was added Pd catalyst (10% on carbon, 60 mg) and the resulting reaction mixture was stirred under H2 at 60 psi for overnight. After the solids were removed by filtration over Celite, the solvent was removed in vacuo to afford 4-(2-amino-5-tert-butyl-1H-pyrrole-3-carbonyl)-3,3-dimethylpiperazin-2-one 7 as a yellow film (100 mg, 92%).

Workup

  1. customthe resulting reaction mixture
  2. customAfter the solids were removed by filtration over Celite
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-51c3ecd5f60144d39cf31500a3d542e9
Source dataset
uspto-grants-2010_06
Patent number
US07741479B2

Reaction notes

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