HCID 69133294, compound → HCID 12109204, compound

HRID 1182045Notes

Reaction equation

HRID 1182045 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[C:16]2[NH:21][C:20](=[O:22])[C:19](=[CH:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:26][N:25]=3)[NH:18][C:17]2=[O:38])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.O.[Zn]>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH:16]2[NH:21][C:20](=[O:22])[CH:19]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:26][N:25]=3)[NH:18][C:17]2=[O:38])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 69133294HCID 69133294, compound2×

Product 1

HCID 12109204HCID 12109204, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A suspension of 3,6-di[(5-benzyloxypyridin-2-yl)methylidene]piperazine-2,5-dione (Compound 10; 0.2 g) and excess of zinc powder in a mixture of 10 mL of acetic acid and 10 mL of water was stirred and refluxed for 5-10 minutes and filtered while hot. Water was added to dissolve zinc acetate. The filtrate was concentrated and filtered. The solid thus obtained was collected and washed with water to give 80 mg (40%) of the desired 3,6-di[(5-benzyloxypyridin-2-yl)methyl]piperazine-2,5-dione (Compound 13).

Workup

  1. temperaturerefluxed for 5-10 minutes
  2. filtrationfiltered while hot
  3. additionWater was added
  4. dissolutionto dissolve zinc acetate
  5. concentrationThe filtrate was concentrated
  6. filtrationfiltered
  7. customThe solid thus obtained
  8. customwas collected
  9. washwashed with water

Sources & evidence

ORD record
ord-e890f67b3d77489a9e8472495edf9f6f
Source dataset
uspto-grants-2007_10
Patent number
US07288545B2

Reaction notes

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