Methane → HCID 178437855, compound

HRID 1597870Notes

Reaction equation

HRID 1597870 reaction equation
[CH:1]1([N:6]2[C:10]([NH2:11])=[C:9]([C:12]([NH2:14])=[O:13])[C:8]([CH2:15][CH3:16])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:17]([C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1)([O-:19])=[O:18].CS(O)(=O)=O.C>C(O)C>[CH:1]1([N:6]2[C:10]3=[N:11][C:24]([C:23]4[CH:26]=[CH:27][C:20]([N+:17]([O-:19])=[O:18])=[CH:21][CH:22]=4)=[N:14][C:12](=[O:13])[C:9]3=[C:8]([CH2:15][CH3:16])[NH:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 297MethaneHCID 5414-NitrobenzaldehydeHCID 6395Methanesulfonic AcidHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178437855HCID 178437855, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (2.0 g, 9 mmol) , 4-nitrobenzaldehyde (2.04 g, 13.5 mmol), methanesulfonic acid (0.25 ml) and xylenes (50 ml) was heated at reflux overnight, followed by an additional 6 hours. Ethanol (200 ml) was added to the reaction mixture, which was then refluxed and then treated with DARCO®. The reaction mixture was filtered, concentrated to 100 ml and then cooled. Yellow needles formed, which were collected by filtration and washed with ether to afford 0.53 g (17%) of 1-cyclopentyl-3-ethyl-6-(4-nitrophenyl)pyrazolo [3,4-d]pyrimidin-4-one, m.p. 321°-323° C. (dec.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperaturewas then refluxed
  4. filtrationThe reaction mixture was filtered
  5. concentrationconcentrated to 100 ml
  6. temperaturecooled
  7. customYellow needles formed
  8. filtrationwhich were collected by filtration
  9. washwashed with ether

Sources & evidence

ORD record
ord-3c71b29a38ad43ada94ebc535c03592d
Source dataset
uspto-grants-1998_04
Patent number
US05736548

Reaction notes

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