Sodium Methoxide → N-[3-(5-amino-1-methylpyrazol-4-yl)propyl]formamide

HRID 349524Notes

Reaction equation

HRID 349524 reaction equation
Cl.Cl.[NH2:3][C:4]1[N:8]([CH3:9])[N:7]=[CH:6][C:5]=1[CH2:10][CH2:11][CH2:12][NH2:13].[CH3:14][O-:15].[Na+]>CO>[NH2:3][C:4]1[N:8]([CH3:9])[N:7]=[CH:6][C:5]=1[CH2:10][CH2:11][CH2:12][NH:13][CH:14]=[O:15]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 179620333-(5-Amino-1-methylpyrazol-4-yl)propylamine dihydrochloride

Product 1

HCID 17962035N-[3-(5-amino-1-methylpyrazol-4-yl)propyl]formamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 3-(5-amino-1-methylpyrazol-4-yl)propylamine dihydrochloride (9.3 g, 40 mmol) in methanol (80 ml) was added 28% sodium methoxide solution in methanol (15.9 g). The mixture was filtered through Celite, and the filtrate was concentrated in vacuo. A solution of the oily residue in ethyl formate (60 g) was stirred under reflux for 20 hours. After cooling, to the reaction mixture was added chloroform. The mixture was filtered through Celite, and the filtrate was concentrated in vacuo. The residue was triturated with ethyl acetate and dried in vacuo to give N-[3-(5-amino-1-methylpyrazol-4-yl)propyl]formamide (6.7 g) as a solid.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. temperatureunder reflux for 20 hours
  4. temperatureAfter cooling, to the reaction mixture
  5. additionwas added chloroform
  6. filtrationThe mixture was filtered through Celite
  7. concentrationthe filtrate was concentrated in vacuo
  8. customThe residue was triturated with ethyl acetate
  9. customdried in vacuo

Sources & evidence

ORD record
ord-b3c889fb70a4440abb23ef21c5cfa33c
Source dataset
uspto-grants-2007_02
Patent number
US07179801B2

Reaction notes

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