N-{5-[3-(2-chloro-phenyl)-4-cyano-pyrrol-1-yl]-2-nitro-phenyl}-3-(3-cyano-phenyl)-3-oxo-propionamide → 4-(2-Chloro-phenyl)-1-[2-(3-cyano-phenyl)-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-7-yl]-1H-pyrrole-3-carbonitrile

HRID 1266832Notes

Reaction equation

HRID 1266832 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]([C:13]#[N:14])=[CH:11][N:10]([C:15]2[CH:16]=[CH:17][C:18]([N+:35]([O-])=O)=[C:19]([NH:21][C:22](=[O:34])[CH2:23][C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]#[N:33])[CH:27]=3)=O)[CH:20]=2)[CH:9]=1>C1COCC1.O.[Fe].CC(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]([C:13]#[N:14])=[CH:11][N:10]([C:15]2[CH:16]=[CH:17][C:18]3[N:35]=[C:24]([C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([C:32]#[N:33])[CH:27]=4)[CH2:23][C:22](=[O:34])[NH:21][C:19]=3[CH:20]=2)[CH:9]=1

Participants

4

Reactant 1

HCID 18548747N-{5-[3-(2-chloro-phenyl)-4-cyano-pyrrol-1-yl]-2-nitro-phenyl}-3-(3-cyano-phenyl)-3-oxo-propionamide

Product 1

HCID 185488524-(2-Chloro-phenyl)-1-[2-(3-cyano-phenyl)-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-7-yl]-1H-pyrrole-3-carbonitrile

Reagents, catalysts & solvents 2

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

Procedure

The title compound was prepared from N-{5-[3-(2-chloro-phenyl)-4-cyano-pyrrol-1-yl]-2-nitro-phenyl}-3-(3-cyano-phenyl)-3-oxo-propionamide (Example M6) 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 (164 mg).

Sources & evidence

ORD record
ord-76df9fdaa5dd4873a7b7343629cbeea2
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

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