Propylamine → N-[3-Methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinolin-4-yl]-N-propylamine

HRID 498011Notes

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.[CH2:22]([NH2:25])[CH2:23][CH3:24]>O>[CH3:15][C:14]1[C:3]2[C:4](=[N:5][C:6]3[C:11]([C:2]=2[NH:25][CH2:22][CH2:23][CH3:24])=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[N:13]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline (1.47 g, 5.00 mmol) and propylamine (2.96 g, 50.0 mmol) was heated and stirred at 100° C. for 6 hours in a sealed stainless tube. The solution was allowed to cool 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 sodium sulfate, and evaporated under reduced pressure. The residue thus obtained was purified by basic silica gel column chromatography (hexane:ethyl acetate=1:1), and the resulting crystals were recrystallized from ethyl acetate/hexane to give the title compound (1.14 g, 72% yield).

Workup

temperaturewas heated
temperatureto cool to room temperature
extractionthe organic matter was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customevaporated under reduced pressure
customThe residue thus obtained
customwas purified by basic silica gel column chromatography (hexane:ethyl acetate=1:1)
customthe resulting crystals were recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record: ord-f17486085ccc492c89affa76f8efdda9
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949648B2

Reaction notes

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