Dimethyl Sulfoxide → 1-ethyl-6-bromo-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

HRID 1586169Notes

Reaction equation

HRID 1586169 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15](Cl)=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([Br:17])=[CH:11][CH:10]=3)[CH3:2].[CH:18]1([CH2:24][NH2:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.CS(C)=O.[NH4+].[OH-]>O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:25][CH2:24][CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([Br:17])=[CH:11][CH:10]=3)[CH3:2]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 14923Ammonium HydroxideHCID 76688CyclohexanemethylamineHCID 195922191-ethyl-4-chloro-6-bromo-1H-pyrazolo[3,4-b]quinoline

Product 1

HCID 212177211-ethyl-6-bromo-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amineYield 98.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1-ethyl-4-chloro-6-bromo-1H-pyrazolo[3,4-b]quinoline (6.5 g, 0.021 mol), cyclohexanemethylamine (5.46 g, 0.042 mol) and DMSO (20 ml) is heated at 110° C. overnight. The reaction mixture is cooled, poured into water and basified with NH4OH. The mixture is extracted with CH2Cl2 (2×100 ml), and the combined CH2Cl2 extracts are washed with brine, then evaporated to about 20 ml. The solution is purified by column chromatography on silica gel eluting with ethyl acetate to afford 8.0 g (98.8%) of 1-ethyl-6-bromo-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, m.p. 158°-160° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionThe mixture is extracted with CH2Cl2 (2×100 ml)
  3. washthe combined CH2Cl2 extracts are washed with brine
  4. customevaporated to about 20 ml
  5. customThe solution is purified by column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-89eca68f49aa40be9894015cd2e91651
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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