Methanol → HCID 22320174, compound

HRID 498009Notes

Reaction equation

HRID 498009 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

4

Reactant 3

HCID 887MethanolHCID 6329MethylamineHCID 223201094-Chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline

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 in methanol (21 mL, 0.27 mol) was heated under reflux at 100° C. for 4 hours in a sealed stainless tube. The solution was allowed to cool to room temperature, and concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (chloroform:methanol=98:2) to give 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 solvent was evaporated 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. temperatureto cool to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue thus obtained
  4. customwas purified by silica gel column chromatography (chloroform:methanol=98:2)

Sources & evidence

ORD record
ord-133a653014e2411a9c4f15b83ddf41f5
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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