Diisopropylethylamine → (S)-methyl 3-(2-methylpiperidin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate
Reaction equation
Cl[C:2]1[C:3](=[O:16])[NH:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2.[CH3:17][C@H:18]1[CH2:23][CH2:22][CH2:21][CH2:20][NH:19]1.CCN(C(C)C)C(C)C>CS(C)=O>[CH3:17][C@H:18]1[CH2:23][CH2:22][CH2:21][CH2:20][N:19]1[C:2]1[C:3](=[O:16])[NH:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (150 mg, 0.63 mmol) in DMSO (2 mL) was added (S)-2-methylpiperidine (166 mg, 1.7 mmol) and DIEA (217 mg, 1.7 mmol). The resulting solution was stirred for 3 hours at 80° C. and then quenched by the addition of water (250 mL), extracted with dichloromethane (3×100 mL), dried over anhydrous sodium sulfate, and then concentrated under vacuum to give a residue, which was purified via silica gel column chromatography (9% ethyl acetate in petroleum ether) to afford (S)-methyl 3-(2-methylpiperidin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as white solid (165 mg, 87%).
Workup
- customquenched by the addition of water (250 mL)
- extractionextracted with dichloromethane (3×100 mL)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under vacuum
- customto give a residue, which
- customwas purified via silica gel column chromatography (9% ethyl acetate in petroleum ether)
Sources & evidence
- ORD record
- ord-e360567f0c6b41cf99b7bc99c435a888
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08912188B2
Reaction notes
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