HCID 178502677, compound → 3-amino-N-methoxy-N-methyl-1H-pyrazole-5-carboxamide

HRID 407782Notes

Reaction equation

HRID 407782 reaction equation
[CH3:1][O:2][N:3]([CH3:14])[C:4]([C:6]1[NH:10][N:9]=[C:8]([N+:11]([O-])=O)[CH:7]=1)=[O:5]>[Pd].CO>[NH2:11][C:8]1[CH:7]=[C:6]([C:4]([N:3]([O:2][CH3:1])[CH3:14])=[O:5])[NH:10][N:9]=1

Participants

4

Reactant 1

HCID 178502677HCID 178502677, compound

Product 1

HCID 645248193-amino-N-methoxy-N-methyl-1H-pyrazole-5-carboxamideYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 250-mL single-neck round-bottomed flask was purged with nitrogen and charged with 150a (16.0 g, 1.0 eq., 80.0 mmol), 10% palladium on carbon (50% wet, 800 mg), and methanol (100 mL). The mixture was evacuated, charged with hydrogen gas, and stirred under hydrogen atmosphere at room temperature overnight. The hydrogen was then evacuated and nitrogen was charged into the flask. The catalyst was removed by filtration through a pad of CELITE®. The filtrate was concentrated under reduced pressure to afford 150b (11.0 g, 81%) as a white solid. MS-ESI: [M+H]+ 171.1

Workup

  1. customA 250-mL single-neck round-bottomed flask was purged with nitrogen
  2. customThe mixture was evacuated
  3. additioncharged with hydrogen gas
  4. customThe hydrogen was then evacuated
  5. additionnitrogen was charged into the flask
  6. customThe catalyst was removed by filtration through a pad of CELITE®
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-53d77faf17414ac18320b8501b016319
Source dataset
uspto-grants-2014_06
Patent number
US08754077B2

Reaction notes

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