Ethanol → 4-(3-Iodo-phenyl)-8-pyrrol-1-yl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

HRID 1266834Notes

Reaction equation

HRID 1266834 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH2:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH:23]=[CH:22][CH:21]=[CH:20]3)=[CH:15][C:14]=2[N+:24]([O-])=O)=O)C=C[CH:7]=1.O.O.Cl[Sn]Cl.[CH3:33][CH2:34][OH:35]>>[I:1][C:2]1[CH:7]=[C:9]([C:10]2[CH2:33][C:34](=[O:35])[NH:24][C:14]3[CH:15]=[C:16]([N:19]4[CH:20]=[CH:21][CH:22]=[CH:23]4)[CH:17]=[CH:18][C:13]=3[N:12]=2)[CH:8]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 61436Stannous chloride dihydrateHCID 18548906HCID 18548906, compound

Product 1

HCID 185487204-(3-Iodo-phenyl)-8-pyrrol-1-yl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Procedure

The title compound was prepared from 3-(3-iodo-phenyl)-N-(2-nitro-4-pyrrol-1-yl-phenyl)-3-oxo-propionamide (Example M8) by reductive cyclization with SnCl2.2H2O in EtOH at 70° C. according to the general procedure J (method b). Obtained as an olive solid (624 mg).

Sources & evidence

ORD record
ord-21740e4ff4df4f7bac0b2748849982b9
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

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