Cyclohexylamine → HCID 15290745, compound

HRID 1720256Notes

Reaction equation

HRID 1720256 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]3[CH:14]=[N:13][NH:12][C:10]3=2)[N:5]=[C:4]([CH3:15])[CH:3]=1.[CH:16]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>>[CH:16]1([NH:22][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]4[CH:14]=[N:13][NH:12][C:10]4=3)[N:5]=[C:4]([CH3:15])[CH:3]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

3

Reactant 2

HCID 7965CyclohexylamineHCID 10443354HCID 10443354, compound

Product 1

HCID 15290745HCID 15290745, compoundYield 68%

Procedure

9-Chloro-7-methyl-1H-pyrazolo[3,4-f]quinoline (0.44 g, 2.0 mmol) and cyclohexylamine (0.79 g, 8.0 mmol) were placed in a sealable reaction vessel which was flushed with nitrogen and then sealed. The reaction was placed in a ° C. bath and heated overnight. The excess cyclohexylamine was removed by rotary evaporation and the residue dissolved in methanol and treated with decolorizing carbon. After filtration through diatomaceous earth (Celite™), the methanol was removed by rotary evaporation and the residue partitioned between ethyl acetate and aqueous potassium hydroxide (KOH). The organic layer was washed with water and dried over sodium sulfate (Na2SO4), and the solvent was removed by rotary evaporation to give a white solid. The solid was washed with ether giving 9-(cyclohexylamino)-7-methyl-1H-pyrazolo[3,4-f]quinoline as white needles (0.38 g, 68%). The free base was converted to the corresponding hydrochloride salt by treatment with anhydrous hydrogen chloride (HCl)/ether.

Workup

  1. customwhich was flushed with nitrogen
  2. customsealed
  3. temperaturebath and heated overnight
  4. customThe excess cyclohexylamine was removed by rotary evaporation
  5. dissolutionthe residue dissolved in methanol
  6. additiontreated with decolorizing carbon
  7. filtrationAfter filtration through diatomaceous earth (Celite™)
  8. customthe methanol was removed by rotary evaporation
  9. customthe residue partitioned between ethyl acetate and aqueous potassium hydroxide (KOH)
  10. washThe organic layer was washed with water
  11. dry with materialdried over sodium sulfate (Na2SO4)
  12. customthe solvent was removed by rotary evaporation
  13. customto give a white solid
  14. washThe solid was washed with ether

Sources & evidence

ORD record
ord-47b71b8ced0d4f61b090773cb9345121
Source dataset
uspto-grants-1996_04
Patent number
US05506235

Reaction notes

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