3,5-Dimethyl-1H-pyrazole-1-carboxamidine mononitrate → Anagrelide

HRID 1706785Notes

Reaction equation

HRID 1706785 reaction equation
C(O[C:4](=[O:17])[CH2:5][NH:6][CH2:7][C:8]1[C:13]([Cl:14])=[C:12]([Cl:15])[CH:11]=[CH:10][C:9]=1[NH2:16])C.[N+]([O-])(O)=O.C[C:23]1C=C(C)N(C(N)=N)[N:24]=1>C(O)C>[Cl:14][C:13]1[C:12]([Cl:15])=[CH:11][CH:10]=[C:9]2[C:8]=1[CH2:7][N:6]1[CH2:5][C:4](=[O:17])[NH:24][C:23]1=[N:16]2

Participants

4

Reactant 2

HCID 1981863,5-Dimethyl-1H-pyrazole-1-carboxamidine mononitrateHCID 9814186Ethyl 2-((6-amino-2,3-dichlorobenzyl)amino)acetate

Product 1

HCID 135409400AnagrelideYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-(2-amino-5,6-dichlorobenzyl)glycine ethyl ester (2.77 g, 0.01 mole) and 3,5-dimethylpyrazole-1-carboxamidine nitrate (2.01 g, 0.01 mole) in absolute ethanol (30 ml) was heated at reflux for 24 hours. The mixture was filtered and the product was washed successively with ethanol, acetone and ether to yield the title compound (1.02 g, 40%); identical (ir, nmr) with authentic material prepared by a prior art procedure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. filtrationThe mixture was filtered
  4. washthe product was washed successively with ethanol, acetone and ether

Sources & evidence

ORD record
ord-15419da330bb41f1b79f03ddfa6f7e2d
Source dataset
uspto-grants-1980_06
Patent number
US04208521

Reaction notes

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