Water → HCID 178461434, compound

HRID 1943912Notes

Reaction equation

HRID 1943912 reaction equation
[CH3:1][C@H:2]1[CH2:4][C@H:3]1[C:5]1[CH:9]=[C:8]([NH2:10])[NH:7][N:6]=1.O.[N+:12]([CH:15]([CH:18]=O)[CH:16]=O)([O-:14])=[O:13].[Na].O>CC(O)=O>[CH3:1][C@H:2]1[CH2:4][C@H:3]1[C:5]1[C:9]2[C:8](=[N:10][CH:16]=[C:15]([N+:12]([O-:14])=[O:13])[CH:18]=2)[NH:7][N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 71317419Sodium nitromalonaldehyde hydrateHCID 178461432HCID 178461432, compound

Product 1

HCID 178461434HCID 178461434, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-(cis-2-Methylcyclopropyl)-1H-pyrazol-5-amine (0.0742 g, 0.541 mmol) and sodium nitromalonaldehyde hydrate (0.0892 g, 0.568 mmol) were heated in AcOH at 90° C. overnight. Water was added, and the precipitate was collected by filtration. This solid was taken up in water as a slurry and heated to reflux for two days. The solution was cooled to room temperature, and the resulting crystals were collected by filtration. The mother liquor was extracted with DCM (3×), dried over Na2SO4 and concentrated to a solid, which was combined with the crystals to provide 3-(cis-2-methylcyclopropyl)-5-nitro-1H-pyrazolo[3,4-b]pyridine (42 mg, 65%) as a solid.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. temperatureheated
  3. temperatureto reflux for two days
  4. filtrationthe resulting crystals were collected by filtration
  5. extractionThe mother liquor was extracted with DCM (3×)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to a solid, which

Sources & evidence

ORD record
ord-f6606afbf864457aa7e50b01d0497ee7
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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