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

HRID 593062Notes

Reaction equation

HRID 593062 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 287a (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 287b (11.0 g, 81%) as 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-ffb5ae198de54218a01d5adb9dda8378
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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