Phosphorus oxychloride → 2-(4-(2-chlorophenyl)-5-((E)-2-(5-(2-methoxypyridin-4-yl)-1,3,4-oxadiazol-2-yl)vinyl)-4H-1,2,4-triazol-3-yl)-5-ethoxypyridine

HRID 509581Notes

Reaction equation

HRID 509581 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([NH:11]C(=O)/C=C\C(O)=O)=[O:10])[CH:6]=[CH:5][N:4]=1.O=P(Cl)(Cl)Cl.[NH2:24][NH:25][C:26]([C:35]1[CH:40]=[CH:39][C:38]([O:41][CH2:42][CH3:43])=[CH:37][N:36]=1)=[N:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[Cl:34]>C1(C)C=CC=CC=1>[Cl:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[N:27]1[C:6](/[CH:7]=[CH:8]/[C:3]2[O:10][C:9]([C:7]3[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[CH:8]=3)=[N:11][N:4]=2)=[N:24][N:25]=[C:26]1[C:35]1[CH:40]=[CH:39][C:38]([O:41][CH2:42][CH3:43])=[CH:37][N:36]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 67958827(Z)-4-(2-methoxypyridine-4-carboamido)-4-oxobut-2-enoic acidHCID 67958932N-amino-N'-(2-chlorophenyl)-5-ethoxy-pyridine-2-carboxamidine

Product 1

HCID 573787392-(4-(2-chlorophenyl)-5-((E)-2-(5-(2-methoxypyridin-4-yl)-1,3,4-oxadiazol-2-yl)vinyl)-4H-1,2,4-triazol-3-yl)-5-ethoxypyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of (Z)-4-(2-methoxypyridine-4-carboamido)-4-oxobut-2-enoic acid 9 (0.30 g, mmol) in 20 mL of PhMe was added 0.5 mL of POCl3. The mixture was stirred at reflux for 2 h. After removal of solvent, the residue was dissolved in 20 mL of dichloromethane and added to 240 mg (0.68 mmol) of N-amino-N′-(2-chlorophenyl)-5-ethoxy-pyridine-2-carboxamidine 5. The mixture was stirred at ambient temperature for 2 h. After removal of solvent, the residue was suspended in 20 mL of PhMe and refluxed for 3 h. After removal of solvent, the residue was purified by column (0-5% of methanol in dichloromethane) to give 2-(4-(2-chlorophenyl)-5-((E)-2-(5-(2-methoxypyridin-4-yl)-1,3,4-oxadiazol-2-yl)vinyl)-4H-1,2,4-triazol-3-yl)-5-ethoxypyridine as a solid. Yield: 20 mg, 3.5%.

Workup

  1. temperatureat reflux for 2 h
  2. customAfter removal of solvent
  3. dissolutionthe residue was dissolved in 20 mL of dichloromethane
  4. stirringThe mixture was stirred at ambient temperature for 2 h
  5. customAfter removal of solvent
  6. temperaturerefluxed for 3 h
  7. customAfter removal of solvent
  8. customthe residue was purified by column (0-5% of methanol in dichloromethane)

Sources & evidence

ORD record
ord-f0adf0d81bce4c6a8beed70bb351bd3b
Source dataset
uspto-grants-2015_08
Patent number
US09096587B2

Reaction notes

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