N'-Hydroxypyridine-4-carboximidamide → 4-[5-(3,4-Bis-benzyloxy-5-nitro-phenyl)-[1,2,4]oxadiazol-3-yl]-pyridine

HRID 1401280Notes

Reaction equation

HRID 1401280 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([N+:26]([O-:28])=[O:27])[C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:12](O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:30]=[C:31]([C:33]1[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=1)[NH2:32]>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:12]2[O:13][N:32]=[C:31]([C:33]3[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=3)[N:30]=2)[CH:15]=[C:16]([N+:26]([O-:28])=[O:27])[C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 15326N'-Hydroxypyridine-4-carboximidamideHCID 462019253,4-Bis(benzyloxy)-5-nitrobenzoic acid

Product 1

HCID 670371464-[5-(3,4-Bis-benzyloxy-5-nitro-phenyl)-[1,2,4]oxadiazol-3-yl]-pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3,4-dibenzyloxy-5-nitrobenzoic acid (0.5 g, 1.32 mmol) in dimethylformamide (5 mL) at room temperature was added 1,1-carbonyldiimidazole (0.246 g, 1.52 mmol) in one portion. After stirring for one hour, N′-hydroxypyridine-4-carboximidamide (0.208 g, 1.52 mmol) was added in one portion and the resulting mixture was stirred at room temperature overnight. The mixture was then stirred at 110° C. for three hours and then allowed to cool to room temperature. The mixture was poured onto ice-water (100 mL) and extracted with 20% isopropanol/dichloromethane. The organic extracts were washed with water and brine, then dried (Na2SO4), filtered and evaporated to leave a solid residue that was recrystallised from ethanol. 4-[5-(3,4-Bis-benzyloxy-5-nitro-phenyl)-[1,2,4]oxadiazol-3-yl]-pyridine was obtained as a beige solid (0.395 g, 62%).

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. stirringThe mixture was then stirred at 110° C. for three hours
  3. additionThe mixture was poured onto ice-water (100 mL)
  4. extractionextracted with 20% isopropanol/dichloromethane
  5. washThe organic extracts were washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customto leave a solid residue that
  10. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-d58d83796971472d9e18b5ce54fbeed4
Source dataset
uspto-grants-2014_12
Patent number
US08907099B2

Reaction notes

Loading…