Stannous chloride dihydrate → 3-(4-Oxo-7-pyrrol-1-yl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-benzonitrile

HRID 1266831Notes

Reaction equation

HRID 1266831 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][CH:22]=[CH:21]3)[CH:17]=[CH:16][C:15]=2[N+:25]([O-])=O)=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2].O.O.Cl[Sn]Cl>CCO>[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:25][C:15]2[CH:16]=[CH:17][C:18]([N:20]3[CH:24]=[CH:23][CH:22]=[CH:21]3)=[CH:19][C:14]=2[NH:13]1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 185488583-(3-cyano-phenyl)-N-(2-nitro-5-pyrrol-1-yl-phenyl)-3-oxo-propionamide

Product 1

HCID 185489173-(4-Oxo-7-pyrrol-1-yl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Alternatively, the title compound was also prepared from (3-(3-cyano-phenyl)-N-(2-nitro-5-pyrrol-1-yl-phenyl)-3-oxo-propionamide (Example M4) by reductive cyclization with SnCl2.2H2O in EtOH at 70° C. according to the general procedure J (method b). Obtained as an olive solid (161 mg).

Sources & evidence

ORD record
ord-e3fdd6cff84a469f9327407334c51bd1
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

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