N-Methylisopropylamine → Methyl 3-(isopropyl(methyl)amino)-7-methoxy-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

HRID 1403590Notes

Reaction equation

Cl[C:2]1[C:3](=[O:18])[NH:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[C:7]([O:16][CH3:17])[CH:6]=2.C[CH2:20][N:21](C(C)C)[CH:22]([CH3:24])[CH3:23].CNC(C)C>CS(C)=O>[CH:22]([N:21]([CH3:20])[C:2]1[C:3](=[O:18])[NH:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[C:7]([O:16][CH3:17])[CH:6]=2)([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of methyl 3-chloro-7-methoxy-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (1.2 g, 4.47 mmol) in DMSO (20 mL) was added DIEA (1.16 g, 8.98 mmol) and methyl(propan-2-yl)amine (490 mg, 6.70 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 3-(isopropyl(methyl)amino)-7-methoxy-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a light yellow solid (1.0 g, 73%).

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-48a5f121e746404fb5f47a011e376517
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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