3,5-Dimethyl-1H-pyrazole-1-carboxamidine mononitrate → HCID 178512456, compound

HRID 356993

Reaction equation

HRID 356993 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][CH:14]=1.C(=O)(O)[O-].[Na+].[N+]([O-])(O)=O.CC1C=C(C)[N:35]([C:39](N)=[NH:40])N=1>C(O)C>[NH:1]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][CH:14]=1)[C:39]([NH2:40])=[NH:35]

Participants

5

Reactant 3

HCID 1981863,5-Dimethyl-1H-pyrazole-1-carboxamidine mononitrateHCID 516892Sodium BicarbonateHCID 545367025-Amino-3-(quinol-4-ylmethylene)-2-oxindole

Product 1

HCID 178512456HCID 178512456, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-amino-3-(quinol-4-ylmethylene)-2-oxindole (2.873 g, 10 mmol) and sodium bicarbonate (0.168 g, 2 mmol) in refluxing ethanol (100 ml) was treated with 3,5-dimethylpyrazole-1-carboxamidine nitrate (3.018 g, 15 mmol) for 20 h. The solvent was removed from the cooled solution, and the residue was chromatographed on silica gel with gradient elution (1 to 5% EtOH in CHCl3) to afford pure title compound in about 50% yield.

Workup

  1. customThe solvent was removed from the cooled solution
  2. customthe residue was chromatographed on silica gel with gradient elution (1 to 5% EtOH in CHCl3)

Sources & evidence

ORD record
ord-7890455eca6b429790257fe619eb8860
Source dataset
uspto-grants-1998_11
Patent number
US05840745

Linked notes

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