3-(3-Cyano-phenyl)-N-[2-nitro-5-(3-phenyl-pyrrol-1-yl)-phenyl]-3-oxo-propionamide → 3-[4-Oxo-7-(3-phenyl-pyrrol-1-yl)-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl]-benzonitrile

HRID 1266839Notes

Reaction equation

HRID 1266839 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]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:21]3)[CH:17]=[CH:16][C:15]=2[N+:31]([O-])=O)=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2]>C1COCC1.O.[Fe].CC(O)=O>[O:12]=[C:11]1[CH2:10][C:9]([C:5]2[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=2)[C:1]#[N:2])=[N:31][C:15]2[CH:16]=[CH:17][C:18]([N:20]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:21]3)=[CH:19][C:14]=2[NH:13]1

Participants

4

Reactant 1

HCID 185487693-(3-Cyano-phenyl)-N-[2-nitro-5-(3-phenyl-pyrrol-1-yl)-phenyl]-3-oxo-propionamide

Product 1

HCID 185487383-[4-Oxo-7-(3-phenyl-pyrrol-1-yl)-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl]-benzonitrile

Reagents, catalysts & solvents 2

HCID 45051903EisenazetatCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

The title compound was prepared from 3-(3-cyano-phenyl)-N-[2-nitro-5-(3-phenyl-pyrrol-1-yl)-phenyl]-3-oxo-propionamide (Example M12) by reductive cyclization with Fe/HOAc in THF/H2O at 80° C. according to the general procedure J (method d). Obtained as a yellow solid (11 mg).

Sources & evidence

ORD record
ord-007b141cb7304eaa8e410040cb9e41f0
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

Loading…