Phosphorus oxychloride → 4-(5-((E)-2-(4-(2-chlorophenyl)-5-(4-(methylsulfonyl)phenyl)-4H-1,2,4-triazol-3-yl)vinyl)-1,3,4-oxadiazol-2-yl)-2-methoxypyridine

HRID 509571Notes

Reaction equation

HRID 509571 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](=[N:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[Cl:44])[C:27]1[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=1>C1(C)C=CC=CC=1>[Cl:44][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=1[N:37]1[C:26]([C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:34])=[O:35])=[CH:29][CH:28]=2)=[N:25][N:24]=[C:6]1/[CH:7]=[CH:8]/[C:3]1[O:10][C:9]([C:7]2[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[CH:8]=2)=[N:11][N:4]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 67958481N-amino-N'-(2-chlorophenyl)-4-methylsulfonyl-benzamidineHCID 67958827(Z)-4-(2-methoxypyridine-4-carboamido)-4-oxobut-2-enoic acid

Product 1

HCID 573785034-(5-((E)-2-(4-(2-chlorophenyl)-5-(4-(methylsulfonyl)phenyl)-4H-1,2,4-triazol-3-yl)vinyl)-1,3,4-oxadiazol-2-yl)-2-methoxypyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of (Z)-4-(2-methoxypyridine-4-carboamido)-4-oxobut-2-enoic acid 9 (180 mg, 0.68 mmol) in 20 mL of PhMe was added 0.2 mL of POCl3. The mixture was stirred at reflux for 2 hours. After removal of solvent, the residue was dissolved in 20 mL of THF and 220 mg (0.68 mmol) of N-amino-N′-(2-chlorophenyl)-4-methylsulfonyl-benzamidine 5 added. The mixture was stirred at ambient temperature for 18 hours. After removal of solvent, the residue was purified by column (0-5% of methanol in dichloromethane) to give 4-(5-((E)-2-(4-(2-chlorophenyl)-5-(4-(methylsulfonyl)phenyl)-4H-1,2,4-triazol-3-yl)vinyl)-1,3,4-oxadiazol-2-yl)-2-methoxypyridine as a solid. Yield: 30 mg, 8.3%.

Workup

  1. temperatureat reflux for 2 hours
  2. customAfter removal of solvent
  3. dissolutionthe residue was dissolved in 20 mL of THF
  4. stirringThe mixture was stirred at ambient temperature for 18 hours
  5. customAfter removal of solvent
  6. customthe residue was purified by column (0-5% of methanol in dichloromethane)

Sources & evidence

ORD record
ord-f9f30d9c7f4b41dc892da489ef26ee3f
Source dataset
uspto-grants-2015_08
Patent number
US09096587B2

Reaction notes

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