Morpholine → HCID 22320347, compound

HRID 498013Notes

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.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:15][C:14]1[C:3]2[C:4](=[N:5][C:6]3[C:11]([C:2]=2[N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[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 solution of 4-chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline (1.47 g, 5.00 mmol), morpholine (0.87 g, 10.0 mmol) and potassium carbonate (1.38 g, 10.0 mmol) in N,N-dimethylformamide (20 mL) was heated under reflux at 100° C. for 12 hours. The solution was cooled to room temperature, and concentrated under reduced pressure. The residue was poured into water and organic matter was extracted with chloroform. 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:chloroform=3:1) to give the title compound (0.63 g, 36% yield).

Workup

temperatureThe solution was cooled to room temperature
concentrationconcentrated under reduced pressure
additionThe residue was poured into water and organic matter
extractionwas extracted with chloroform
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:chloroform=3:1)

Sources & evidence

ORD record: ord-1ecd3b6276fb4c16ae8e660904f6e729
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949648B2

Reaction notes

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