1,1'-Carbonyldiimidazole → 1-Ethyl-6-[((2-(morpholin-4-yl)ethyl)amino)methyl]imidazo[1,2-a]-quinoxalin-4(5H)-one
Reaction equation
CO[C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6](F)[C:5]=1[N+:11]([O-])=O.C([N:34]1[CH:38]=[C:37]([CH2:39][CH3:40])[N:36]=[CH:35]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[NH2:41][CH2:42][CH2:43][N:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1.[C:50](N1C=CN=C1)(N1C=CN=C1)=[O:51].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[CH2:39]([C:37]1[N:36]2[C:6]3[C:5]([NH:11][C:50](=[O:51])[C:35]2=[N:34][CH:38]=1)=[C:4]([CH2:3][NH:41][CH2:42][CH2:43][N:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1)[CH:9]=[CH:8][CH:7]=3)[CH3:40]Participants
6
Reactant 5
Product 1
Procedure
Treat 3-fluoro-2-nitrobenzoic acid methylester with 1-trityl-4-ethyl imidazole, followed by treatment with 4-(2-aminoethyl)morpholine and catalytic hydrogenation cyclization with carbonyldiimidazole, followed by reduction with lithium aluminum hydride to provide the title compound.
Sources & evidence
- ORD record
- ord-2a21fcb0d2dd432fba0de968cefbf835
- Source dataset
- uspto-grants-1991_10
- Patent number
- US05055465
Reaction notes
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