4-Chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline → HCID 22320332, compound

HRID 497964Notes

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.O1CCCC1.[CH3:27][NH:28][CH3:29]>O>[CH3:27][N:28]([CH3:29])[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

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 tetrahydrofuran (5.00 mL, 10.0 mmol) solution, and the mixture was heated at 100° C. overnight in a sealed tube. The reaction mixture was cooled to room temperature and poured into water, and organic matter was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was 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

temperatureThe reaction mixture was cooled to room temperature
extractionwas extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue thus obtained
customwas purified by silica gel column chromatography (ethyl acetate to ethyl acetate:methanol=9:1)

Sources & evidence

ORD record: ord-d9ddb6e1e5fa45debe62beb1c0d15864
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949648B2

Reaction notes

Loading…