Ammonium formate → Methyl 4-amino-5-carbamoyl-1-(2-ethoxyethyl)-1h-pyrazole-3-carboxylate

HRID 2401303Notes

Reaction equation

HRID 2401303 reaction equation
[C:1]([C:4]1[N:8]([CH2:9][CH2:10][O:11][CH2:12][CH3:13])[N:7]=[C:6]([C:14]([O:16][CH3:17])=[O:15])[C:5]=1[N+:18]([O-])=O)(=[O:3])[NH2:2].C([O-])=O.[NH4+]>CO.[OH-].[Pd+2].[OH-]>[NH2:18][C:5]1[C:6]([C:14]([O:16][CH3:17])=[O:15])=[N:7][N:8]([CH2:9][CH2:10][O:11][CH2:12][CH3:13])[C:4]=1[C:1](=[O:3])[NH2:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 58935581Methyl 5-carbamoyl-1-(2-ethoxyethyl)-4-nitro-1h-pyrazole-3-carboxylate

Product 1

HCID 58935554Methyl 4-amino-5-carbamoyl-1-(2-ethoxyethyl)-1h-pyrazole-3-carboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Palladium (II) hydroxide (100 mg) was added to a solution of the nitro compound of step 3 (970 mg, 3.39 mmol) in methanol (20 mL) and the mixture warmed to reflux. Ammonium formate (1.07 g, 16.97 mmol) was added and the reaction mixture stirred at reflux for 2 hours. The catalyst was removed by filtration through Arbocel® and the reaction mixture concentrated in vacuo to yield the amide product.

Workup

  1. temperaturethe mixture warmed to reflux
  2. temperatureat reflux for 2 hours
  3. customThe catalyst was removed by filtration through Arbocel®
  4. concentrationthe reaction mixture concentrated in vacuo

Sources & evidence

ORD record
ord-0d502c78805140fd821237abb2f3a4e6
Source dataset
uspto-grants-2014_08
Patent number
US08796287B2

Reaction notes

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