Diisopropylethylamine → (S)-methyl 3-(2-methylpiperidin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

HRID 1403361Notes

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.CCN(C(C)C)C(C)C.[CH3:26][C@H:27]1[CH2:32][CH2:31][CH2:30][CH2:29][NH:28]1>CS(C)=O>[CH3:26][C@H:27]1[CH2:32][CH2:31][CH2:30][CH2:29][N:28]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]=2

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (500 mg, crude) in DMSO (6 mL) was added DIEA (543 mg, 4.20 mmol), (2S)-2-methylpiperidine (104 mg, 1.05 mmol). The solution was stirred for 6 h at 100° C. Then the reaction was quenched by the addition of water (50 mL). The resulting solution was extracted with ethyl acetate (4×30 mL) and the organic layers were concentrated under vacuum. The residue was purified by a silica gel column with 1%-5% ethyl acetate in petroleum ether to afford methyl 3-[(2S)-2-methylpiperidin-1-yl]-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a yellow solid (98 mg).

Workup

customThen the reaction was quenched by the addition of water (50 mL)
extractionThe resulting solution was extracted with ethyl acetate (4×30 mL)
concentrationthe organic layers were concentrated under vacuum
customThe residue was purified by a silica gel column with 1%-5% ethyl acetate in petroleum ether

Sources & evidence

ORD record: ord-0f3b0e77f5194dfba59501bdb6f893ed
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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