HCID 54269484, compound → HCID 54424075, compound

HRID 1599080Notes

Reaction equation

HRID 1599080 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[N:33]=[CH:32][CH:31]=[CH:30][N: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: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[N:29]=[CH:30][CH:31]=[CH:32][N:33]=2)[C:4]1=[O:34]

Participants

4

Reactant 1

HCID 54269484HCID 54269484, compound

Product 1

HCID 54424075HCID 54424075, compoundYield 60.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 2-[2,4-dioxo-3-(phenyl-hydrazono)-5-pyrimidin-2-yl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepine-1-yl]-N-isopropyl-N-(4-methoxy-phenyl)-acetamide (500 mg, 0.886 mmol) in acetic acid (12 mL) at ambient temperature was added zinc dust (530 mg) and the resulting mixture was stirred 1 h. The zinc was separated by filtration, the filtrate concentrated in vacuo, and the resultant oil partitioned between water (30 mL) and ethyl acetate (80 mL). The pH was adjusted to 8 with 6N sodium hydroxide and the phases were separated. The aqueous phase was extracted with ethyl acetate (2×35 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 (15 g) eluting with methylene chloride/methanol (19:1, 250 ml). Appropriate fractions were combined and concentrated to give the title compound (255 mg, 0.537 mmol) as a white glass:

Workup

  1. customThe zinc was separated by filtration
  2. concentrationthe filtrate concentrated in vacuo
  3. customthe resultant oil partitioned between water (30 mL) and ethyl acetate (80 mL)
  4. customthe phases were separated
  5. extractionThe aqueous phase was extracted with ethyl acetate (2×35 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 (15 g)
  11. washeluting with methylene chloride/methanol (19:1, 250 ml)
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-cb3fb22c35964083b06395ff05b28f52
Source dataset
uspto-grants-1998_04
Patent number
US05739129

Reaction notes

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