1-Ethyl-1H-pyrazol-5-amine → HCID 69182067, compound

HRID 2373237Notes

Reaction equation

HRID 2373237 reaction equation
[CH:1]1([CH:7]=[C:8]([C:13]([CH:15]2[CH2:17][CH2:16]2)=O)[C:9]([O:11][CH3:12])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:18]([N:20]1[C:24]([NH2:25])=[CH:23][CH:22]=[N:21]1)[CH3:19]>C(O)(C)(C)C>[CH:1]1([C:7]2[C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:13]([CH:15]3[CH2:17][CH2:16]3)[N:25]=[C:24]3[N:20]([CH2:18][CH3:19])[N:21]=[CH:22][C:23]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 3373101-Ethyl-1H-pyrazol-5-amineHCID 69182024HCID 69182024, compound

Product 1

HCID 69182067HCID 69182067, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of methyl 3-cyclohexyl-2-(cyclopropylcarbonyl)acrylate (6.01 g) and 1-ethyl-1H-pyrazol-5-amine (2.97 mg) in tert-BuOH (60 ml) was refluxed for 22 hours. The solvent was evaporated off, and the residue was dissolved in dioxane (60 ml). To the mixture was added 4,5-dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile (5.77 g). The mixture was stirred for 6 h at room temperature. The mixture was filtered off, and the filtrate was evaporated. The residue was dissolved in EtOAc (20 ml), and to the solution was added silicagel, followed by hexanes (100 ml). The mixture was filtered, and filter cake was washed with EtOAc-hexanes (1-5). The filtrate was evaporated off. Silicagel column chromatography (EtOAc-hexanes, a linear gradient of EtOAc from 0 to 15%) afforded methyl 4-cyclohexyl-6-cyclopropyl-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate as a colorless oil, which was crystallized upon standing (4.36 g).

Workup

  1. temperaturewas refluxed for 22 hours
  2. customThe solvent was evaporated off
  3. dissolutionthe residue was dissolved in dioxane (60 ml)
  4. additionTo the mixture was added 4,5-dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile (5.77 g)
  5. filtrationThe mixture was filtered off
  6. customthe filtrate was evaporated
  7. dissolutionThe residue was dissolved in EtOAc (20 ml)
  8. additionto the solution was added silicagel
  9. filtrationThe mixture was filtered
  10. filtrationfilter cake
  11. washwas washed with EtOAc-hexanes (1-5)
  12. customThe filtrate was evaporated off

Sources & evidence

ORD record
ord-6ba7b130629b464ea3e42f94c7714077
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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