HCID 66958833, compound → HCID 57717511, compound

HRID 1360482Notes

Reaction equation

HRID 1360482 reaction equation
[CH2:1]([N:3]1[C:15]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:14]2[C:5]([C:6]([NH2:24])=[N:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=32)=[N:4]1)[CH3:2]>FC(F)(F)C(O)=O.C(#N)C.[Pt](=O)=O>[CH:18]1([CH2:17][CH2:16][C:15]2[N:3]([CH2:1][CH3:2])[N:4]=[C:5]3[C:14]=2[C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[N:7]=[C:6]3[NH2:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 1

HCID 66958833HCID 66958833, compound

Product 1

HCID 57717511HCID 57717511, compoundYield 53.8%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 6342AcetonitrileSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 2-ethyl-1-(2-phenylethyl)-2H-pyrazolo[3,4-c]quinolin-4-amine (prepared as described in Example 41, 575 mg, 1.81 mmol) and platinum (IV) oxide (290 mg) in trifluoroacetic acid (8 mL) was shaken under hydrogen pressure (50 psi, 3.4×105 Pa) for 22.5 hours on a Parr apparatus. The reaction mixture was filtered through a poly(tetrafluoroethylene) membrane to remove the catalyst. The filtrate was concentrated under reduced pressure. The crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution using 0-30% CMA in chloroform) and the appropriate fractions were concentrated to yield a solid that was slurried in hot acetonitrile. The mixture was allowed to cool to ambient temperature with stirring, then 318 mg of 1-(2-cyclohexylethyl)-2-ethyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-4-amine was isolated as a white powder, mp 177.0-179.0° C.

Workup

  1. filtrationThe reaction mixture was filtered through a poly(tetrafluoroethylene) membrane
  2. customto remove the catalyst
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution using 0-30% CMA in chloroform)
  5. concentrationthe appropriate fractions were concentrated
  6. customto yield a solid
  7. stirringwith stirring

Sources & evidence

ORD record
ord-7310317091cb42b2996aa2a3f469e9b5
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

Loading…