4-Chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline → HCID 22320174, compound

HRID 497963Notes

Reaction equation

HRID 497963 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.CO.[CH3:24][NH2:25]>>[CH3:24][NH:25][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

Participants

3

Reactant 2

HCID 223201094-Chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinolineHCID 57454252Monomethylamine methanol

Product 1

HCID 22320174HCID 22320174, compound

Conditions

Temperature
100 °C

Procedure

A solution of 4-chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline (0.8 g, 2.71 mmol) in 40% methylamine methanol (21 mL, 0.27 mol) solution was heated and stirred at 100° C. for 4 hours in a sealed stainless tube. After the solution was cooled to room temperature, the reaction solvents were evaporated under reduced pressure. Purification of the residue thus obtained by silica gel column chromatography (chloroform:methanol=98:2) gave an oil of N-methyl-N-[3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinolin-4-yl]amine. To a solution of the oil in ethanol (10 mL), was added a saturated hydrochloric acid/ethanol solution (10 mL), and the solution was concentrated under reduced pressure. The residue thus obtained was recrystallized from methanol/ethyl acetate to give the title compound (0.63 g, 64% yield).

Workup

  1. temperatureAfter the solution was cooled to room temperature
  2. customthe reaction solvents were evaporated under reduced pressure
  3. customPurification of the residue
  4. customthus obtained by silica gel column chromatography (chloroform:methanol=98:2)

Sources & evidence

ORD record
ord-41da07c3a9d146d7b95d91f99a3a6d8f
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

Loading…