1,1'-Carbonyldiimidazole → 2-Ethoxycarbonyl-8-(1-imidazolyl)-I-methylimidazo[1,2-a]quinoxalin-4(5H)-one

HRID 1599432Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[CH:4][C:3]=1[N:13]1[C:17]([CH3:18])=[C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:15]=[CH:14]1.[C:24](N1C=CN=C1)(N1C=CN=C1)=[O:25]>ClC1C=CC=CC=1Cl>[CH2:22]([O:21][C:19]([C:16]1[N:15]=[C:14]2[C:24](=[O:25])[NH:1][C:2]3[C:3](=[CH:4][C:5]([N:8]4[CH:12]=[CH:11][N:10]=[CH:9]4)=[CH:6][CH:7]=3)[N:13]2[C:17]=1[CH3:18])=[O:20])[CH3:23]

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 1-(2-amino-5-(1-imidazolyl)phenyl)-4-ethoxycarbonyl-5-methyl-1H-imidazole (1.0 g, 3.2 mmol), 1,1'-carbonyldiimidazole (2.6 g, 16.0 mmol) in 1,2-dichlorobenzene (50 ml) was stirred at 180° C. for 16 h under N2. The precipitate was filtered off and submitted to flash chromatography on silica gel 60 eluting with dichloromethane/methanol (4:1) to give 400 mg (37%) of the title compound. M.p. >250° C.

Workup

filtrationThe precipitate was filtered off

Sources & evidence

ORD record: ord-2ea78a60681d4e07830312e4b6e34bb6
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05741785

Reaction notes

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