N-Methylisopropylamine → Methyl 7-fluoro-3-[methyl(propan-2-yl)amino]-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

HRID 1403605Notes

Reaction equation

Cl[C:2]1[C:3](=[O:17])[NH:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[C:7]([F:16])[CH:6]=2.C[CH2:19][N:20](C(C)C)[CH:21]([CH3:23])[CH3:22].CNC(C)C>CS(C)=O>[F:16][C:7]1[CH:6]=[C:5]2[C:10]([N:11]=[C:2]([N:20]([CH3:19])[CH:21]([CH3:23])[CH3:22])[C:3](=[O:17])[NH:4]2)=[CH:9][C:8]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of methyl 3-chloro-7-fluoro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (2.0 g, crude) in DMSO (20 ml) was added DIEA (2.0 g, 15.48 mmol) and methyl(propan-2-yl)amine (790 mg, 10.80 mmol) with stirring at 85° C. overnight. The reaction mixture was cooled to room temperature. The product was precipitated by the addition water and the solids were collected by filtration to afford methyl 7-fluoro-3-[methyl(propan-2-yl)amino]-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a light yellow solid (800 mg).

Workup

temperatureThe reaction mixture was cooled to room temperature
customThe product was precipitated by the addition water
filtrationthe solids were collected by filtration

Sources & evidence

ORD record: ord-92cd2a867c9f4fdf89caa8548441c7e0
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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