1-[(5,6-Dimethyl-2-methoxypyrazin-3-yl)aminocarbonyl]-4-(3,5-dinitrophenyl)piperazine → 1-[(5,6-Dimethyl-2-methoxypyrazin-3-yl)aminocarbonyl]-4-(3,5-diaminophenyl)piperazine

HRID 1841460Notes

Reaction equation

HRID 1841460 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[C:24]([N+:26]([O-])=O)[CH:23]=[C:22]([N+:29]([O-])=O)[CH:21]=3)[CH2:16][CH2:15]2)=[O:13])[C:5]([O:9][CH3:10])=[N:6][C:7]=1[CH3:8]>C(O)C.[Pd]>[CH3:1][C:2]1[N:3]=[C:4]([NH:11][C:12]([N:14]2[CH2:15][CH2:16][N:17]([C:20]3[CH:25]=[C:24]([NH2:26])[CH:23]=[C:22]([NH2:29])[CH:21]=3)[CH2:18][CH2:19]2)=[O:13])[C:5]([O:9][CH3:10])=[N:6][C:7]=1[CH3:8]

Participants

4

Reactant 1

HCID 234461841-[(5,6-Dimethyl-2-methoxypyrazin-3-yl)aminocarbonyl]-4-(3,5-dinitrophenyl)piperazine

Product 1

HCID 234462501-[(5,6-Dimethyl-2-methoxypyrazin-3-yl)aminocarbonyl]-4-(3,5-diaminophenyl)piperazineYield 45%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-[(5,6-Dimethyl-2-methoxypyrazin-3-yl)aminocarbonyl]-4-(3,5-dinitrophenyl)piperazine was dissolved in ethanol (30 ml) and thereto 10% palladium/carbon (10 mg) was added. The resulting mixture was hydrogenated for 4 hours, and then filtered to remove the 10% palladium/carbon. The filtrate was concentrated and purified by column chromatography to obtain the titled compound.

Workup

  1. filtrationfiltered
  2. customto remove the 10% palladium/carbon
  3. concentrationThe filtrate was concentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-d9fc24a4a239432ca9b90dbcd4ad2a72
Source dataset
uspto-grants-2004_01
Patent number
US06683184B2

Reaction notes

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