1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-carbonitrile → 7,7'-azanediylbis(methylene)bis(1-ethyl-3,3,5-trimethyl-1H-benzo[b][1,4]diazepine-2,4-dione)
Reaction equation
[CH2:1]([N:3]1[C:9](=[O:10])[C:8]([CH3:12])([CH3:11])[C:7](=[O:13])[N:6]([CH3:14])[C:5]2[CH:15]=[C:16]([C:19]#[N:20])[CH:17]=[CH:18][C:4]1=2)[CH3:2]>[Pd].C(O)(=O)C>[NH:20]([CH2:19][C:16]1[CH:17]=[CH:18][C:4]2[N:3]([CH2:1][CH3:2])[C:9](=[O:10])[C:8]([CH3:11])([CH3:12])[C:7](=[O:13])[N:6]([CH3:14])[C:5]=2[CH:15]=1)[CH2:19][C:16]1[CH:17]=[CH:18][C:4]2[N:3]([CH2:1][CH3:2])[C:9](=[O:10])[C:8]([CH3:12])([CH3:11])[C:7](=[O:13])[N:6]([CH3:14])[C:5]=2[CH:15]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
10% Palladium on carbon(0.3 g) was added to an acetic acid solution (20 ml) of 1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-carbonitrile(1.4 g), and catalytic reduction was carried out at room temperature under 4 atm. The catalyst was removed by celite filtration, followed by concentration under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate: methanol=9:1→5:5). The purified product was condensed under reduced pressure to give the title compound(0.19 g) as a colorless oily matter.
Workup
- customwas carried out at room temperature under 4 atm
- customThe catalyst was removed by celite filtration
- concentrationfollowed by concentration under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate: methanol=9:1→5:5)
- customcondensed under reduced pressure
Sources & evidence
- ORD record
- ord-58984af3918f4f9eb9320486fcbee40b
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09212187B2
Reaction notes
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