5-Azido-3-methyl-3,5-dihydro-4H-benzo[d][1,2]diazepin-4-one → 5-Amino-3-methyl-3,5-dihydro-4H-benzo[d][1,2]diazepin-4-one

HRID 2302280Notes

Reaction equation

HRID 2302280 reaction equation
[N:1]([CH:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH:8]=[N:7][N:6]([CH3:15])[C:5]1=[O:16])=[N+]=[N-]>CCOC(C)=O.[Pd]>[NH2:1][CH:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH:8]=[N:7][N:6]([CH3:15])[C:5]1=[O:16]

Participants

4

Reactant 1

HCID 222436965-Azido-3-methyl-3,5-dihydro-4H-benzo[d][1,2]diazepin-4-one

Product 1

HCID 222436975-Amino-3-methyl-3,5-dihydro-4H-benzo[d][1,2]diazepin-4-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 5(R,S)-azido-4,5-dihydro-3-methyl-3H-2,3-benzodiazepin-4-one (1.5 g, 7 mmol) in EtOAc (150 mL) was added 10% Pd on carbon (50 mg) and stirred under an atmosphere of hydrogen. The reaction was closely monitored by TLC using EtOAc as eluent. The reaction was complete after 1 h (TLC) and then filtered the catalyst over a pad of celite. The solvent was removed and the 5(R,S)-amino-4,5-dihydro-3-methyl-3H-2,3-benzodiazepin-4-one was dried under high vacuum. This amine product was used immediately in the coupling reactions with various amino acids to yield Formula IIC products.

Workup

  1. filtration(TLC) and then filtered the catalyst over a pad of celite
  2. customThe solvent was removed
  3. dry with materialthe 5(R,S)-amino-4,5-dihydro-3-methyl-3H-2,3-benzodiazepin-4-one was dried under high vacuum
  4. customto yield Formula IIC products

Sources & evidence

ORD record
ord-ee57af62bfb144d18f0d2bdeffcafcce
Source dataset
uspto-grants-2002_08
Patent number
US06432944B1

Reaction notes

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