2-[2,4-dioxo-5-phenyl-3-(phenylhydrazono)-2,3,4,5-tetrahydro benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-phenylacetamide → 2-(3-amino-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-phenyl-acetamide

HRID 1416115Notes

Reaction equation

HRID 1416115 reaction equation
[O:1]=[C:2]1[N:8]([CH2:9][C:10]([N:12]([CH:19]([CH3:21])[CH3:20])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:11])[C:7]2[CH:22]=[CH:23][CH:24]=[CH:25][C:6]=2[N:5]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:4](=[O:32])[C:3]1=[N:33]NC1C=CC=CC=1>C(O)(=O)C.[Zn]>[NH2:33][CH:3]1[C:2](=[O:1])[N:8]([CH2:9][C:10]([N:12]([CH:19]([CH3:21])[CH3:20])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:11])[C:7]2[CH:22]=[CH:23][CH:24]=[CH:25][C:6]=2[N:5]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:4]1=[O:32]

Participants

4

Reactant 1

HCID 545518192-[2,4-dioxo-5-phenyl-3-(phenylhydrazono)-2,3,4,5-tetrahydro benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-phenylacetamide

Product 1

HCID 101142752-(3-amino-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-phenyl-acetamideYield 100.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

Zinc powder (9.1 g) was added in portions to a slurry of 2-[2,4-dioxo-5-phenyl-3-(phenylhydrazono)-2,3,4,5-tetrahydro benzo[b][1,4]-diazepin-1-yl]-N-isopropyl-N-phenylacetamide (7.5 g), in glacial acetic acid, cooled to 0° C. The reaction was allowed to warm to R.T. and stirred an additional hour. The zinc was filtered through a celite pad and the glacial acetic acid was evaporated in vacuo. The residue was dissolved in ethyl acetate (200 ml) and washed with 10% aqueous sodium carbonate (2×100 ml) and water (2×100 ml), dried (Na2SO4) and evaporated to a tan oil. Trituration with hexane and ethyl acetate provided the title compound as a light tan powder (6.3 g). 1H-NMR (300 MHz, CDCl3): d 7.6-6.8 (m, 14H), 5.05 (m, 1H), 4.3-4.0 (m, 3H) 1.05 (d, 6H); MS (FAB)=448 (MH+); TLC, Rf =0.25 (chloroform:methanol, 9:1).

Workup

  1. temperatureto warm to R.T.
  2. filtrationThe zinc was filtered through a celite pad
  3. customthe glacial acetic acid was evaporated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (200 ml)
  5. washwashed with 10% aqueous sodium carbonate (2×100 ml) and water (2×100 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated to a tan oil

Sources & evidence

ORD record
ord-f93d4f5963bc41fba35ffc88608eb60c
Source dataset
uspto-grants-1999_06
Patent number
US05910495

Reaction notes

Loading…