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

HRID 375885Notes

Reaction equation

HRID 375885 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) was heated at 110° C. overnight. The reaction mixture was cooled, poured into water and basified with NH4OH. The mixture was extracted with CH2Cl2 (2×100 ml) and the combined CH2Cl2 extracts were washed with brine, then evaporated to about 20 ml. The solution was 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 was cooled
  2. extractionThe mixture was extracted with CH2Cl2 (2×100 ml)
  3. washthe combined CH2Cl2 extracts were washed with brine
  4. customevaporated to about 20 ml
  5. customThe solution was purified by column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-c8a961def5b94fb1b79515683903592c
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

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