3,5-Dimethyl-1H-pyrazole-1-carboxamidine mononitrate → HCID 178514396, compound

HRID 487049Notes

Reaction equation

HRID 487049 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH:5]([P:14]([O:19]CC)(=[O:18])[O:15]CC)[P:6]([O:11]CC)(=[O:10])[O:7]CC.[N+]([O-])(O)=O.C[C:27]1C=C(C)[N:29](C(N)=N)[N:28]=1>CN(C=O)C>[NH2:29][N:28]=[CH:27][NH:1][CH2:2][CH2:3][CH2:4][CH:5]([P:14]([OH:19])(=[O:18])[OH:15])[P:6]([OH:11])(=[O:10])[OH:7]

Participants

4

Reactant 2

HCID 1981863,5-Dimethyl-1H-pyrazole-1-carboxamidine mononitrateHCID 153967084,4-Bis(diethoxyphosphoryl)butan-1-amine

Product 1

HCID 178514396HCID 178514396, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.69 g (2 mmol) of tetraethyl 4-aminobutane-1,1-bisphosphonate (according to DE 3,225,469 A1, 01.05.1984) and 0.402 g (2 mmol) of 3,5-dimethylpyrazole-1-carboxamidine nitrate in 10 ml of DMF is heated at boiling point for 3 hours. The DMF is then distilled off in vacuo and the residue is dissolved in a little water. After extraction with diethyl ether and ethyl acetate (the organic extracts are discarded), the aqueous phase is distilled in vacuo. A dark oil (0.89 g) remains. This is heated at boiling point for 8 hours in 15 ml of concentrated hydrochloric acid. The excess hydrochloric acid is distilled off and the residue is treated with a little water, DMF and acetone. The precipitate is filtered off with suction and dried in vacuo.

Workup

  1. customfor 3 hours
  2. distillationThe DMF is then distilled off in vacuo
  3. dissolutionthe residue is dissolved in a little water
  4. extractionAfter extraction with diethyl ether and ethyl acetate (the organic extracts
  5. distillationis distilled in vacuo
  6. temperatureThis is heated
  7. customfor 8 hours
  8. distillationThe excess hydrochloric acid is distilled off
  9. additionthe residue is treated with a little water, DMF and acetone
  10. filtrationThe precipitate is filtered off with suction
  11. customdried in vacuo

Sources & evidence

ORD record
ord-109a533bafaa492c901fadfc6d27757c
Source dataset
uspto-grants-1994_03
Patent number
US05294608

Reaction notes

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