1-{3-[3-(3-Cyano-phenyl)-3-oxo-propionylamino]-4-nitro-phenyl}-1H-pyrrole-2-carboxylic acid methyl ester → 1-[2-(3-Cyano-phenyl)-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-7-yl]-1H-pyrrole-2-carboxylic acid methyl ester

HRID 1266840Notes

Reaction equation

HRID 1266840 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[C:12]([NH:19][C:20](=[O:32])[CH2:21][C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]#[N:31])[CH:25]=3)=O)[CH:11]=2)[CH:7]=[CH:8][CH:9]=1)=[O:4]>C1COCC1.O.[Fe].CC(O)=O>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:10]2[CH:15]=[CH:14][C:13]3[N:16]=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([C:30]#[N:31])[CH:25]=4)[CH2:21][C:20](=[O:32])[NH:19][C:12]=3[CH:11]=2)[CH:7]=[CH:8][CH:9]=1)=[O:4]

Participants

4

Reactant 1

HCID 865869701-{3-[3-(3-Cyano-phenyl)-3-oxo-propionylamino]-4-nitro-phenyl}-1H-pyrrole-2-carboxylic acid methyl ester

Product 1

HCID 697810311-[2-(3-Cyano-phenyl)-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-7-yl]-1H-pyrrole-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

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

Procedure

The title compound was prepared from 1-{3-[3-(3-cyano-phenyl)-3-oxo-propionylamino]-4-nitro-phenyl}-1H-pyrrole-2-carboxylic acid methyl ester (Example M15) 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 (323 mg).

Sources & evidence

ORD record
ord-72c492f08bce4c5d9b9da1705dc6ea40
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

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