HCID 70656402, compound → HCID 70656943, compound

HRID 68960Notes

Reaction equation

HRID 68960 reaction equation
[CH3:1][N:2]1[C:8](=[O:9])[CH2:7][C:6](=[O:10])[N:5]([CH3:11])[C:4]2[CH:12]=[C:13]([C:16]#[N:17])[CH:14]=[CH:15][C:3]1=2>[Pd].C(O)(=O)C>[NH2:17][CH2:16][C:13]1[CH:14]=[CH:15][C:3]2[N:2]([CH3:1])[C:8](=[O:9])[CH2:7][C:6](=[O:10])[N:5]([CH3:11])[C:4]=2[CH:12]=1

Participants

4

Reactant 1

HCID 70656402HCID 70656402, compound

Product 1

HCID 70656943HCID 70656943, compoundYield 55.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

10% Palladium on carbon (0.1 g) was added to an acetic acid solution (20 ml) of 1,5-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-carbonitrile (0.3 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 (0.17 g) as a yellowish white solid.

Workup

  1. customwas carried out at room temperature under 4 atm
  2. customThe catalyst was removed by celite filtration
  3. concentrationfollowed by concentration under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=9:1→5:5)
  5. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-f499e8a783d94f389895decb2e67981e
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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