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Dimethylamine → HCID 22320332, compound

HRID 498012
Notes
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Reaction equation

HRID 498012 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]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[N:13]=[C:14]([CH3:15])[C:3]=12.[CH3:22][NH:23][CH3:24].O1CCCC1>O>[CH3:22][N:23]([CH3:24])[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]2[N:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[N:13]=[C:14]([CH3:15])[C:3]=12
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 223201094-Chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline

Product 1

HCID 22320332HCID 22320332, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

4-chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline (1.00 g, 3.39 mmol) was added to a 2M dimethylamine in tetrahydrofuran solution (5.00 mL, 10.0 mmol), and the solution was heated under reflux overnight at 100° C. in a sealed tube. The solution was cooled to room temperature and poured into water, and the organic matter was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (ethyl acetate to ethyl acetate:methanol=9:1) to give the title compound (1.00 g, 97% yield).

Workup

  1. temperaturethe solution was heated
  2. temperatureThe solution was cooled to room temperature
  3. extractionthe organic matter was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel column chromatography (ethyl acetate to ethyl acetate:methanol=9:1)

Sources & evidence

ORD record
ord-21b50eb7fb304dc4b11ab7a273df08a0
Source dataset
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06949648B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes