2-[2,4-dioxo-5-phenyl-3-(phenyl-hydrazono)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepine-1-yl]-N-isopropyl-N-(4-methoxy-phenyl)-acetamide → 2-(3-Amino-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo [b] [1,4] diazepine-1-yl)-N-isopropyl-N-(4-methoxy-phenyl)-acetamide

HRID 1416116Notes

Reaction equation

HRID 1416116 reaction equation
[O:1]=[C:2]1[N:8]([CH2:9][C:10]([N:12]([CH:21]([CH3:23])[CH3:22])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[O:11])[C:7]2[CH:24]=[CH:25][CH:26]=[CH:27][C:6]=2[N:5]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:4](=[O:34])[C:3]1=[N:35]NC1C=CC=CC=1>C(O)(=O)C.[Zn]>[NH2:35][CH:3]1[C:2](=[O:1])[N:8]([CH2:9][C:10]([N:12]([CH:21]([CH3:23])[CH3:22])[C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)=[O:11])[C:7]2[CH:24]=[CH:25][CH:26]=[CH:27][C:6]=2[N:5]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:4]1=[O:34]

Participants

4

Reactant 1

HCID 544415272-[2,4-dioxo-5-phenyl-3-(phenyl-hydrazono)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepine-1-yl]-N-isopropyl-N-(4-methoxy-phenyl)-acetamide

Product 1

HCID 537484432-(3-Amino-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo [b] [1,4] diazepine-1-yl)-N-isopropyl-N-(4-methoxy-phenyl)-acetamideYield 71.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 2-[2,4-dioxo-5-phenyl-3-(phenyl-hydrazono)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepine-1-yl]-N-isopropyl-N-(4-methoxy-phenyl)-acetamide (4.28 g) in acetic acid (50 mL) at ambient temperature, was added zinc dust (4.11 g) and stirred three hours. The zinc was filtered off, the filtrate concentrated in vacuo, and the resultant oil partitioned between water (60 mL) and ethyl acetate (100 mL). The pH was adjusted to 8 with 6N sodium hydroxide and the phases separated. The aqueous phase was extracted with ethyl acetate (2×75 mL) and the organics combined, dried with magnesium sulfate, filtered and concentrated in vacuo to give a yellow foam. The crude product was purified via flash chromatography on silica gel (80 g) eluted successively with ethyl acetate (260 mL) (to remove impurity) and methylene chloride/methanol (19:1, 200 ml) (to elute product). Appropriate fractions were combined and concentrated to give the title compound (2.58 g) as a yellow foam.

Workup

  1. filtrationThe zinc was filtered off
  2. concentrationthe filtrate concentrated in vacuo
  3. customthe resultant oil partitioned between water (60 mL) and ethyl acetate (100 mL)
  4. customthe phases separated
  5. extractionThe aqueous phase was extracted with ethyl acetate (2×75 mL)
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a yellow foam
  10. customThe crude product was purified via flash chromatography on silica gel (80 g)
  11. washeluted successively with ethyl acetate (260 mL) (to remove impurity) and methylene chloride/methanol (19:1, 200 ml) (to elute product)
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-841829c75b884966b752543472cc6ae0
Source dataset
uspto-grants-1999_06
Patent number
US05910495

Reaction notes

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