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

HRID 1266838Notes

Reaction equation

HRID 1266838 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]([CH2:25][OH:26])=[CH:21]3)[CH:17]=[CH:16][C:15]=2[N+:27]([O-])=O)=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2]>C1COCC1.O.[Fe].CC(O)=O>[OH:26][CH2:25][C:22]1[CH:23]=[CH:24][N:20]([C:18]2[CH:17]=[CH:16][C:15]3[N:27]=[C:9]([C:5]4[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=4)[C:1]#[N:2])[CH2:10][C:11](=[O:12])[NH:13][C:14]=3[CH:19]=2)[CH:21]=1

Participants

4

Reactant 1

HCID 185488653-(3-Cyano-phenyl)-N-[5-(3-hydroxymethyl-pyrrol-1-yl)-2-nitro-phenyl]-3-oxo-propionamide

Product 1

HCID 185488883-[7-(3-Hydroxymethyl-pyrrol-1-yl)-4-oxo-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-[5-(3-hydroxymethyl-pyrrol-1-yl)-2-nitro-phenyl]-3-oxo-propionamide (Example M11) by reductive cyclization with Fe/HOAc in THF/H2O at 60° C. according to the general procedure J (method d). Obtained as a brown solid (18 mg).

Sources & evidence

ORD record
ord-a103d7afee6749c79f9bdab1955f87f6
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

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