Cyclohexanemethylamine → 1-ethyl-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

HRID 1586130Notes

Reaction equation

HRID 1586130 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]2[N:12]([CH2:15][CH3:16])[N:13]=[CH:14][C:3]=12.[CH:17]1([CH2:23][NH2:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>CS(C)=O>[CH2:15]([N:12]1[C:4]2=[N:5][C:6]3[C:11]([C:2]([NH:24][CH2:23][CH:17]4[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)=[C:3]2[CH:14]=[N:13]1)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH3:16]

Participants

4

Reactant 2

HCID 76688CyclohexanemethylamineHCID 158169081-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline

Product 1

HCID 99047131-ethyl-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amineYield 90.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture of 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]quinoline (10 g, 0.043 mol) and DMSO (75 ml) is added cyclohexanemethylamine (10.75 g, 0.095 mol). The reaction mixture is refluxed for about four hours, then is allowed to stand for about 2 days. About 40-50 ml of the DMSO is removed in vacuo and the residue is pured into ice waterl. A precipitate forms which is collected by filtration, washed with water and dried. The PG,13 solid precipitate is dissolved in CH2Cl2, washed with water, then brine and is then dried over MgSO4. The solvent is filtered and concentrated in vacuo and the residue is purified by column chromatography on silica gel eluting with ethyl acetate/cyclohexane (3/7) followed by recrystallization from hexane to afford 12 g (90.2%) of 1-ethyl-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, as light yellow crystals, m.p. 161°-163° C.

Workup

  1. temperatureThe reaction mixture is refluxed for about four hours
  2. customAbout 40-50 ml of the DMSO is removed in vacuo
  3. filtrationA precipitate forms which is collected by filtration
  4. washwashed with water
  5. customdried
  6. dissolutionThe PG,13 solid precipitate is dissolved in CH2Cl2
  7. washwashed with water
  8. dry with materialbrine and is then dried over MgSO4
  9. filtrationThe solvent is filtered
  10. concentrationconcentrated in vacuo
  11. customthe residue is purified by column chromatography on silica gel eluting with ethyl acetate/cyclohexane (3/7)
  12. customfollowed by recrystallization from hexane

Sources & evidence

ORD record
ord-f410396aab3544fe8a5371348b314dd6
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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