Potassium Carbonate → 5-chloro-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)pyridine

HRID 1478101Notes

Reaction equation

HRID 1478101 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]([Cl:41])=[CH:37][N:36]=1)=[N:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[Cl:34].C([O-])([O-])=O.[K+].[K+]>CC#N>[Cl:41][C:38]1[CH:39]=[CH:40][C:35]([C:26]2[N:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[Cl:34])[C:6](/[CH:7]=[CH:8]/[C:3]3[O:10][C:9]([C:7]4[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[CH:8]=4)=[N:11][N:4]=3)=[N:24][N:25]=2)=[N:36][CH:37]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 67958768N-amino-5-chloro-N'-(2-chlorophenyl)pyridine-2-carboxamidineHCID 67958827(Z)-4-(2-methoxypyridine-4-carboamido)-4-oxobut-2-enoic acid

Product 1

HCID 573785075-chloro-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)pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a suspension of (Z)-4-(2-methoxypyridine-4-carboamido)-4-oxobut-2-enoic acid 4 (0.2 g, 0.75 mmol) in CH3CN was added POCl3 (0.37 g, 2.4 mmol). The mixture was stirred under reflux for 16 hours, cooled to ambient temperature and concentrated under reduced pressure. The residue was dissolved in CH3CN, treated with a solution of N-amino-5-chloro-N′-(2-chlorophenyl)pyridine-2-carboxamidine 8 (0.38 g, 1.2 mmol) in CH3CN and K2CO3 (0.38 g, 1.2 mmol). The mixture was stirred at ambient temperature for 1 hour, refluxed for 2 hours, and filtered. The filtrate was concentrated. The residue was subjected to FCC (50-60% EtOAc/hexanes) to afford the title compound 5-chloro-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)pyridine as a white solid. Yield: 0.11 g, 28%.

Workup

  1. temperatureunder reflux for 16 hours
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in CH3CN
  4. stirringThe mixture was stirred at ambient temperature for 1 hour
  5. temperaturerefluxed for 2 hours
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-de0d6bd9684b42e5a507609922ad7725
Source dataset
uspto-grants-2016_08
Patent number
US09403812B2

Reaction notes

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