Triethylamine → N,N,1-trimethyl-1H-pyrazole-4-carboxamide

HRID 1802271Notes

Reaction equation

HRID 1802271 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[CH:4]=[N:3]1.[CH2:10]([N:12](CC)[CH2:13]C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.CNC>CN(C=O)C>[CH3:10][N:12]([CH3:13])[C:7]([C:5]1[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=1)=[O:9]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 6431601-Methyl-1H-pyrazole-4-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 59551573N,N,1-trimethyl-1H-pyrazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl-1H-pyrazole-4-carboxylic acid (1.0 g, 7.93 mmol) was combined with DMF (10.0 ml) to give a light yellow solution. Triethylamine (3.3 ml, 23.8 mmol) and 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate (2.8 g, 8.72 mmol) were added. The reaction mixture was set under argon and stirred for 1 h at RT. Then dimethylamine hydrochloride (679 mg, 8.33 mmol) was added. The reaction mixture was stirred over night. The solvent was evaporated and the residue was absorbed on silica gel and chromatographed (amine silica gel cartridge, CH2Cl2). The resulting brown oil was dried at the HV over night. Yield: 1.16 g (96%); brown oil; MS: m/z=154.1 [M+H]+.

Workup

  1. customto give a light yellow solution
  2. stirringThe reaction mixture was stirred over night
  3. customThe solvent was evaporated
  4. customthe residue was absorbed on silica gel
  5. customchromatographed (amine silica gel cartridge, CH2Cl2)
  6. customThe resulting brown oil was dried at the HV over night

Sources & evidence

ORD record
ord-7052bce9aa1e439ca487024c77df2979
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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