HCID 57750722, compound → 1-[(4-amino-2-ethyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]cyclohexanol

HRID 549254Notes

Reaction equation

HRID 549254 reaction equation
[NH2:1][C:2]1[C:11]2=[N:12][N:13]([CH2:23][CH3:24])[C:14]([CH2:15][C:16]3([OH:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[C:10]2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1>FC(F)(F)C(O)=O.[Pt](=O)=O>[NH2:1][C:2]1[C:11]2=[N:12][N:13]([CH2:23][CH3:24])[C:14]([CH2:15][C:16]3([OH:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[C:10]2[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

4

Reactant 1

HCID 57750722HCID 57750722, compound

Product 1

HCID 119506771-[(4-amino-2-ethyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]cyclohexanolYield 37%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

1-[(4-Amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]cyclohexanol (0.226 g, 0.70 mmol) and platinum(IV) oxide (0.107 g, 0.47 mmol) were slurried in trifluoroacetic acid (10 mL). The flask was degassed three times and charged to 50 psi hydrogen (3.45×105 Pa). After 16 hours, the catalyst was removed via filtration through a bed of CELITE filter agent, rinsing with methanol. The filtrate was concentrated. The oily residue was dissolved in 6N hydrochloric acid (3 mL). The acidic mixture was brought to pH 14 using 50% aqueous sodium hydroxide. The mixture was extracted with 10% methanol in dichloromethane, dried over anhydrous sodium sulfate, and concentrated. The material was purified via automated flash chromatography eluting with a linear gradient of 2-20% CMA in chloroform. The resulting white solid was triturated in acetonitrile and then isolated by filtration to provide 0.085 g of 1-[(4-amino-2-ethyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]cyclohexanol as a white solid, m.p. 232-234° C.

Workup

  1. customThe flask was degassed three times
  2. additioncharged to 50 psi hydrogen (3.45×105 Pa)
  3. customthe catalyst was removed via filtration through a bed of CELITE
  4. filtrationfilter agent
  5. washrinsing with methanol
  6. concentrationThe filtrate was concentrated
  7. dissolutionThe oily residue was dissolved in 6N hydrochloric acid (3 mL)
  8. extractionThe mixture was extracted with 10% methanol in dichloromethane
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated
  11. customThe material was purified via automated flash chromatography
  12. washeluting with a linear gradient of 2-20% CMA in chloroform
  13. customThe resulting white solid was triturated in acetonitrile
  14. customisolated by filtration

Sources & evidence

ORD record
ord-89c5f7b1e546480da2186c40659cf0cd
Source dataset
uspto-grants-2011_05
Patent number
US07943636B2

Reaction notes

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