N-Methylisopropylamine → HCID 70654268, compound

HRID 1405315Notes

Reaction equation

HRID 1405315 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.[CH3:17][NH:18][CH:19]([CH3:21])[CH3:20].CCN(C(C)C)C(C)C>CS(C)=O>[CH3:17][N:18]([CH:19]([CH3:21])[CH3:20])[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

5

Reactant 3

HCID 78485N-MethylisopropylamineHCID 81531DiisopropylethylamineHCID 68194304Methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

Product 1

HCID 70654268HCID 70654268, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (3 g, 12.57 mmol) in DMSO (20 ml) was added methyl(propan-2-yl)amine (1.3 g, 17.77 mmol), and DIEA (3.2 g, 24.76 mmol). The resulting solution was stirred overnight at 70° C. The product was precipitated by the addition of ice/water and collected by filtration to afford methyl 3-[methyl(propan-2-yl)amino]-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a yellow solid (2.5 g, 72%).

Workup

  1. customThe product was precipitated by the addition of ice/water
  2. filtrationcollected by filtration

Sources & evidence

ORD record
ord-0d17bc0b872845899f32b2d56f70187f
Source dataset
uspto-grants-2014_12
Patent number
US08916561B2

Reaction notes

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