Diisopropylethylamine → Methyl 3-(cyclopropyl(methyl)amino)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

HRID 1403327Notes

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.CC[N:19]([CH:23]([CH3:25])[CH3:24])[CH:20](C)C.Cl.CNC1CC1>CS(C)=O>[CH:23]1([N:19]([CH3:20])[C:2]2[C:3](=[O:16])[NH:4][C:5]3[C:10]([N:11]=2)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=3)[CH2:24][CH2:25]1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (1.0 g, 4.20 mmol) in DMSO (6 mL) was added DIEA (1.35 g, 10.47 mmol), and N-methylcyclopropanamine hydrochloride (490 mg, 4.58 mmol). The solution was stirred 10 mins at room temperature and 2 h at 75° C. Then the reaction was quenched by the addition of water (100 mL) and the solids were collected by filtration to afford methyl 3-(cyclopropyl(methyl)amino)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a yellow solid (405 mg, 35%).

Workup

customThen the reaction was quenched by the addition of water (100 mL)
filtrationthe solids were collected by filtration

Sources & evidence

ORD record: ord-25ff86816bac4e1099c31477a1ea482e
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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