Diisopropylethylamine → (S)-methyl 3-(2-methylpyrrolidin-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.CC[N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])C.C[C@H]1CCCN1>CS(C)=O>[CH3:25][C@H:23]1[CH2:24][CH2:22][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
- 100 °C
Procedure
To a solution of methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (500.0 mg, crude) in DMSO (6 mL) was added DIEA (543.0 mg, 4.20 mmol), and (S)-2-methylpyrrolidine (268.0 mg, 3.15 mmol). The solution was stirred for 10 h at 100° C. and then quenched by the addition of water (25 mL), extracted with ethyl acetate (3×80 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by a silica gel column with 1%-5% ethyl acetate in petroleum ether to afford (S)-methyl 3-(2-methylpyrrolidin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a yellow solid (216.0 mg).
Workup
- customquenched by the addition of water (25 mL)
- extractionextracted with ethyl acetate (3×80 mL)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under vacuum
- customThe residue was purified by a silica gel column with 1%-5% ethyl acetate in petroleum ether
Sources & evidence
- ORD record
- ord-a658310ee0c64da998cf24d5c3fad00e
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08912188B2
Reaction notes
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