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

HRID 18934Notes

Reaction equation

HRID 18934 reaction equation
[C:1]([C:5]1[NH:6][C:7]([C:13]([N:15]2[CH2:20][CH2:19][NH:18][C:17](=[O:21])[C:16]2([CH3:23])[CH3:22])=[O:14])=[C:8]([N+:10]([O-])=O)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:10][C:8]1[CH:9]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[NH:6][C:7]=1[C:13]([N:15]1[CH2:20][CH2:19][NH:18][C:17](=[O:21])[C:16]1([CH3:22])[CH3:23])=[O:14]

Participants

4

Reactant 1

HCID 586792724-(2-tert-butyl-4-nitro-1H-pyrrole-5-carbonyl)-3,3-dimethylpiperazin-2-one

Product 1

HCID 586792594-(4-amino-2-tert-butyl-1H-pyrrole-5-carbonyl)-3,3-dimethylpiperazin-2-oneYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of the previously prepared 4-(2-tert-butyl-4-nitro-1H-pyrrole-5-carbonyl)-3,3-dimethylpiperazin-2-one (80 mg, 0.25 mmol) dissolved in methanol (2 mL) and Pd on charcoal (10% w/w, 20 mg) was shaken under hydrogen atmosphere in a Parr shaker at 50 psi for 18 hours. The reaction was filtered through celite, the residue concentrated under vacuum to afford 68 mg of the desired 4-(4-amino-2-tert-butyl-1H-pyrrole-5-carbonyl)-3,3-dimethylpiperazin-2-one as a yellow oil.

Workup

  1. filtrationThe reaction was filtered through celite
  2. concentrationthe residue concentrated under vacuum

Sources & evidence

ORD record
ord-aeba203d1bc24ab79b8a60a2fe020729
Source dataset
uspto-grants-2010_06
Patent number
US07741479B2

Reaction notes

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