Pyrrolidine → Methyl 2-oxo-3-(pyrrolidin-1-yl)-1,2-dihydroquinoxaline-6-carboxylate

HRID 1403422Notes

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.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.CCN(C(C)C)C(C)C>CS(C)=O.O>[O:16]=[C:3]1[C:2]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=2)[NH:4]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (200 mg, 0.84 mmol) in DMSO (2 mL) was added pyrrolidine (90 mg, 1.27 mmol) and DIEA (163 mg, 1.26 mmol). After stirring overnight at 70° C., the reaction mixture was dissolved in water (50 mL), then filtered to afford methyl 2-oxo-3-(pyrrolidin-1-yl)-1,2-dihydroquinoxaline-6-carboxylate as a light yellow solid (200 mg, 87%).

Workup

filtrationfiltered

Sources & evidence

ORD record: ord-c2f1a17ed7fe4390bf05927c66a93629
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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