Acetic Acid → N-(2-(7-bromo-3-(4-methoxyphenyl)-2-oxoquinoxalin-1(2H)-yl)ethyl)acetamide

HRID 1366110Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][NH:12][C:13](=[O:15])[CH3:14].[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24](=O)[C:25](OCC)=[O:26])=[CH:20][CH:19]=1.C(O)(=O)C>C(O)C>[Br:8][C:5]1[CH:4]=[C:3]2[C:2]([N:1]=[C:24]([C:21]3[CH:22]=[CH:23][C:18]([O:17][CH3:16])=[CH:19][CH:20]=3)[C:25](=[O:26])[N:9]2[CH2:10][CH2:11][NH:12][C:13](=[O:15])[CH3:14])=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of crude N-(2-(2-amino-5-bromophenylamino)ethyl)acetamide from Example 14 in ethanol (0.74 mL) 870 mg of ethyl 2-(4-methoxyphenyl)-2-oxoacetate was added. To that mixture acetic acid was added resulting in of 1% v/v AcOH in EtOH solution. The reaction mixture was stirred at 80° C. for 18 h and allowed to cool to room temperature. The yellow precipitate was collected by filtration and washed with two 5 mL portions of EtOH. The yellow solid was dried under vacuum to provide N-(2-(7-bromo-3-(4-methoxyphenyl)-2-oxoquinoxalin-1(2H)-yl)ethyl)acetamide.

Workup

temperatureto cool to room temperature
filtrationThe yellow precipitate was collected by filtration
washwashed with two 5 mL portions of EtOH
customThe yellow solid was dried under vacuum

Sources & evidence

ORD record: ord-61fe8b2a9b254304a88624f598e50811
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893066B2

Reaction notes

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