3-(3-Cyano-phenyl)-N-[5-(3-cyano-4-phenyl-pyrrol-1-yl)-2-nitro-phenyl]-3-oxo-propionamide → 1-[2-(3-Cyano-phenyl)-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-7-yl]-4-phenyl-1H-pyrrole-3-carbonitrile
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9](=O)[CH2:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([N:20]3[CH:24]=[C:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:22]([C:31]#[N:32])=[CH:21]3)[CH:17]=[CH:16][C:15]=2[N+:33]([O-])=O)=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2]>C1COCC1.O.[Fe].CC(O)=O>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH2:10][C:11](=[O:12])[NH:13][C:14]3[CH:19]=[C:18]([N:20]4[CH:24]=[C:23]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[C:22]([C:31]#[N:32])=[CH:21]4)[CH:17]=[CH:16][C:15]=3[N:33]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
The title compound was prepared from 3-(3-cyano-phenyl)-N-[5-(3-cyano-4-phenyl-pyrrol-1-yl)-2-nitro-phenyl]-3-oxo-propionamide (Example M7) by reductive cyclization with Fe/HOAc in THF/H2O at 80° C. according to the general procedure J (method d). Obtained as a brown solid (206 mg).
Sources & evidence
- ORD record
- ord-3a971af3a05e4329b1256bba234d28be
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06548495B2
Reaction notes
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