Water → Methyl 3-(benzyl(methyl)amino)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

HRID 1403530Notes

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.[CH2:17]([NH:24][CH3:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCN(C(C)C)C(C)C.O>CS(C)=O>[CH2:17]([N:24]([CH3:25])[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)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (500 mg, 2.10 mmol) in DMSO (6 mL) was added benzyl(methyl)amine (305 mg, 2.52 mmol), and DIEA (542 mg, 4.19 mmol). The resulting solution was stirred for 2 h at 85° C., then water (50 mL) was added, causing a precipitate to form which was collected by filtration to afford methyl 3-(benzyl(methyl)amino)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a yellow solid (0.55 g, 81%).

Workup

customto form which
filtrationwas collected by filtration

Sources & evidence

ORD record: ord-5f582d65ec884019b96695c5d846e831
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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