Diisopropylethylamine → (R)-methyl 3-(sec-butylamino)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

HRID 1403452Notes

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][C@@H:18]([NH2:21])[CH2:19][CH3:20].CCN(C(C)C)C(C)C>CS(C)=O>[C@H:18]([NH:21][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)([CH2:19][CH3:20])[CH3:17]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (0.5 g, 2.1 mmol) in DMSO (10 mL) was added (R)-butan-2-amine (570 mg, 7.79 mmol) and DIEA (850 mg, 6.58 mmol). The resulting solution was stirred for 4 hours at 70° C. and then quenched by the addition of water (50 mL). The solids were collected by filtration to afford (R)-methyl 3-(sec-butylamino)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a white solid (425 mg, 75%).

Workup

customquenched by the addition of water (50 mL)
filtrationThe solids were collected by filtration

Sources & evidence

ORD record: ord-c8bd401d8de24ae88fd3f1d4cfbacc65
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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