Diisopropylethylamine → (S)-methyl 7-methoxy-3-(2-methylpyrrolidin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

HRID 1403621Notes

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.CC[N:21]([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])C.Cl.CN1CCCC1>CS(C)=O>[CH3:17][O:16][C:7]1[CH:6]=[C:5]2[C:10]([N:11]=[C:2]([N:21]3[CH2:22][CH2:24][CH2:27][C@@H:25]3[CH3:26])[C:3](=[O:18])[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-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 methylpyrrolidine hydrochloride (650 mg, 5.35 mmol), and the reaction was stirred 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 (S)-methyl 7-methoxy-3-(2-methylpyrrolidin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a light yellow solid (1.0 g, 71%).

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-c86bb5458d7e407d9962c258d419fd8d
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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