3,5-Dimethyl-1H-pyrazole-1-carboxamidine mononitrate → HCID 178421247, compound

HRID 725176Notes

Reaction equation

HRID 725176 reaction equation
[NH2:1][CH2:2][CH2:3][O:4]/[N:5]=[CH:6]/[C@@H:7]1[C@:15]2([CH3:16])[C@@:10]([OH:23])([CH2:11][C@@H:12]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13][CH2:14]2)[CH2:9][CH2:8]1.[N+:24]([O-:27])(O)=[O:25].[C:28](N1C(C)=CC(C)=N1)(=[NH:30])[NH2:29]>C(O)C>[N+:24]([O:23][C@@:10]12[CH2:11][C@@H:12]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:13][CH2:14][C@:15]1([CH3:16])[C@@H:7](/[CH:6]=[N:5]/[O:4][CH2:3][CH2:2][NH:1][C:28]([NH2:30])=[NH:29])[CH2:8][CH2:9]2)([O-:27])=[O:25]

Participants

4

Reactant 2

HCID 1981863,5-Dimethyl-1H-pyrazole-1-carboxamidine mononitrateHCID 10958069(1S,3aS,5S,7aR)-1-[(E)-2-aminoethoxyiminomethyl]-7a-methyl-5-phenyl-2,3,4,5,6,7-hexahydro-1H-inden-3a-ol

Product 1

HCID 178421247HCID 178421247, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.75 g of (1S,3aS,5S,7aR)-1-[(E)-2-aminoethoxyimino]methyl-5-phenyl-7a-methylperhydroinden-3a-ol (I-am) and 1.05 g of 1-amidino-3,5-dimethylpirazole nitrate in 20 ml of ethanol was heated at reflux for 10 hrs. The solution was evaporated to dryness under reduced pressure and the residue was purified by flash chromatography (SiO2) with chloroform/methanol/28% ammonium hydroxide 78:20:2 as the eluant. The fractions containing the title compound were collected and evaporated to dryness. The residue was ground with diisopropyl ether:ethanol 9:1 to give 0.42 g of the title compound (I-db) as a white solid.

Workup

  1. temperatureat reflux for 10 hrs
  2. customThe solution was evaporated to dryness under reduced pressure
  3. customthe residue was purified by flash chromatography (SiO2) with chloroform/methanol/28% ammonium hydroxide 78:20:2 as the eluant
  4. additionThe fractions containing the title compound
  5. customwere collected
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-6cca69c1b79941619ad4b8c39b39b19a
Source dataset
uspto-grants-1998_01
Patent number
US05705531

Reaction notes

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