Pyridine → N-(5-cyano-2-pyridyl)-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole-3-yl]-2-methyl benzoic acid amide

HRID 878807Notes

Reaction equation

HRID 878807 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.N1C=CC=CC=1.[Cl:16][C:17]1[CH:18]=[C:19]([C:24]2([C:39]([F:42])([F:41])[F:40])[O:28][N:27]=[C:26]([C:29]3[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[C:31]([CH3:38])[CH:30]=3)[CH2:25]2)[CH:20]=[C:21]([Cl:23])[CH:22]=1>ClCCl>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:33](=[O:34])[C:32]2[CH:36]=[CH:37][C:29]([C:26]3[CH2:25][C:24]([C:19]4[CH:20]=[C:21]([Cl:23])[CH:22]=[C:17]([Cl:16])[CH:18]=4)([C:39]([F:42])([F:41])[F:40])[O:28][N:27]=3)=[CH:30][C:31]=2[CH3:38])=[N:3][CH:4]=1)#[N:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8182602-Amino-5-cyanopyridineHCID 866114794-(5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methylbenzoyl chloride

Product 1

HCID 67164147N-(5-cyano-2-pyridyl)-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole-3-yl]-2-methyl benzoic acid amideYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a solution of 0.39 g of 2-amino-5-cyanopyridine and 0.71 g of pyridine in 20 mL of dichloromethane, a solution of 1.31 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoyl-chloride synthesized in Step 4 of Synthetic Example 1 in 20 mL of dichloromethane was added dropwise. After the completion of the addition dropwise, it was continued to stir at the same temperature further for 1 hour. After the completion of the reaction, the solvent was distilled off under reduced pressure, the residue was dissolved in 50 mL of ethyl acetate, precipitated insoluble material was removed through silica gel column, and the solvent was distilled off under reduced pressure. The residual solid was washed with diisopropyl ether to obtain 1.11 g of the aimed product as colorless resinous substance.

Workup

  1. additionAfter the completion of the addition dropwise
  2. customAfter the completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionthe residue was dissolved in 50 mL of ethyl acetate
  5. customprecipitated insoluble material
  6. customwas removed through silica gel column
  7. distillationthe solvent was distilled off under reduced pressure
  8. washThe residual solid was washed with diisopropyl ether

Sources & evidence

ORD record
ord-f9ccb347df1e46b09bdcec2820cbd804
Source dataset
uspto-grants-2015_03
Patent number
US08987464B2

Reaction notes

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