Dimethylamine, hydrochloride → N,N,1-trimethyl-4-nitropyrazole-3-carboxamide

HRID 467633Notes

Reaction equation

HRID 467633 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([N+:7]([O-:9])=[O:8])[C:4]([C:10]([OH:12])=O)=[N:3]1.[CH3:13][N:14](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)[CH3:15].[B-](F)(F)(F)F.Cl.CNC.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:13][N:14]([CH3:15])[C:10]([C:4]1[C:5]([N+:7]([O-:9])=[O:8])=[CH:6][N:2]([CH3:1])[N:3]=1)=[O:12]

Participants

6

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 5359761-Methyl-4-nitro-1H-pyrazole-3-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 67076071N,N,1-trimethyl-4-nitropyrazole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-methyl-4-nitro-1H-pyrazole-3-carboxylic acid (500 mg, 2.92 mmol) in DMF (5 ml) under inert gas atmosphere was treated with TBTU (1030 mg, 3.2 mmol), dimethylamine hydrochloride (262 mg, 3.2 mmol) and N,N-diisopropylethylamine (2.0 ml, 11.7 mmol) and stirring was continued for 4 h. All volatiles were removed and the crude product was extracted with water and ethyl acetate. The organic phase was washed with sodium bicarbonate and the aqueous phases were back-extracted with ethyl acetate and dichloromethane. The combined organic phases were dried and the solvent was evaporated. The product was obtained after purification by silica gel chromatography using a dichloromethane/methanol gradient as white solid (230 mg, 40%).

Workup

  1. customAll volatiles were removed
  2. extractionthe crude product was extracted with water and ethyl acetate
  3. washThe organic phase was washed with sodium bicarbonate
  4. extractionthe aqueous phases were back-extracted with ethyl acetate and dichloromethane
  5. customThe combined organic phases were dried
  6. customthe solvent was evaporated
  7. customThe product was obtained
  8. customafter purification by silica gel chromatography

Sources & evidence

ORD record
ord-803839c5a5684682adf59b8aa530745e
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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