(4S)-4-(dimethylamino)-1-(1-methyl-4-nitro-1H-pyrazol-3-yl)pyrrolidin-2-one → (4S)-1-(4-amino-1-methyl-1H-pyrazol-3-yl)-4-(dimethylamino)pyrrolidin-2-one

HRID 632782Notes

Reaction equation

HRID 632782 reaction equation
[CH3:1][N:2]([CH3:18])[C@@H:3]1[CH2:7][N:6]([C:8]2[C:12]([N+:13]([O-])=O)=[CH:11][N:10]([CH3:16])[N:9]=2)[C:5](=[O:17])[CH2:4]1>[C].[Pd].CO>[NH2:13][C:12]1[C:8]([N:6]2[CH2:7][C@@H:3]([N:2]([CH3:1])[CH3:18])[CH2:4][C:5]2=[O:17])=[N:9][N:10]([CH3:16])[CH:11]=1

Participants

4

Reactant 1

HCID 118061504(4S)-4-(dimethylamino)-1-(1-methyl-4-nitro-1H-pyrazol-3-yl)pyrrolidin-2-one

Product 1

HCID 118061163(4S)-1-(4-amino-1-methyl-1H-pyrazol-3-yl)-4-(dimethylamino)pyrrolidin-2-oneYield 90.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of (4S)-4-(dimethylamino)-1-(1-methyl-4-nitro-1H-pyrazol-3-yl)pyrrolidin-2-one (69.9 mg), 10% palladium-carbon (24.9 mg) and methanol (1.38 mL) was stirred at room temperature for 1 hr under hydrogen atmosphere. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure to give the title compound (55.6 mg).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-34127cd536934de98677b8d71785aee3
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

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