HCID 616538, compound → 4-methyl-7-Amino-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione

HRID 1844296Notes

Reaction equation

HRID 1844296 reaction equation
[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[C:11]([N+:14]([O-])=O)[CH:12]=[CH:13][C:6]=2[NH:5][C:4](=[O:17])[CH2:3]1.C1COCC1.C(O)C>C(O)C.[Pd]>[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[C:11]([NH2:14])[CH:12]=[CH:13][C:6]=2[NH:5][C:4](=[O:17])[CH2:3]1

Participants

5

Reactant 2

HCID 616538HCID 616538, compoundHCID 21873804Tetrahydrofuran ethanol

Product 1

HCID 104429394-methyl-7-Amino-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dioneYield 30%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Intermediate 1 (3.48 g, 15 mmol, preparation described in Example 1) was suspended in a 120 mL of 1:1 solution of THF/Ethanol. The suspension was treated with nitrogen followed by vacuum, before adding Pd/C 10% (0.7 g), suspended in ethanol. The reaction vessel was then fitted onto the Parr hydrogenator and left under hydrogen pressure (20 psi) for about 3 hours with stirring. The excess hydrogen gas was removed using vacuum and then nitrogen was purged through the solution. The catalyst was filtered off using celite and the filtrate was evaporated to the minimum amount of ethanol. A white precipitate formed which was separated by filtration and dried under vacuum to afford 918 mg of desired material 3 in 30% yield.

Workup

  1. additionThe suspension was treated with nitrogen
  2. customThe reaction vessel was then fitted onto the Parr hydrogenator
  3. customThe excess hydrogen gas was removed
  4. customnitrogen was purged through the solution
  5. filtrationThe catalyst was filtered off
  6. customthe filtrate was evaporated to the minimum amount of ethanol
  7. customA white precipitate formed which
  8. customwas separated by filtration
  9. customdried under vacuum

Sources & evidence

ORD record
ord-6fc89c446d0e44f4a7971d95048c869e
Source dataset
uspto-grants-2015_02
Patent number
US08946410B2

Reaction notes

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