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

HRID 878853Notes

Reaction equation

HRID 878853 reaction equation
N[C:2]1[CH:3]=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[Cl:9][C:10]1[CH:11]=[C:12]([C:17]2([C:32]([F:35])([F:34])[F:33])[O:21][N:20]=[C:19]([C:22]3[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[C:24]([CH3:31])[CH:23]=3)[CH2:18]2)[CH:13]=[C:14]([Cl:16])[CH:15]=1.[N:36]1C=CC=CC=1>>[Cl:8][C:5]1([NH:36][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][C:22]([C:19]3[CH2:18][C:17]([C:12]4[CH:11]=[C:10]([Cl:9])[CH:15]=[C:14]([Cl:16])[CH:13]=4)([C:32]([F:35])([F:34])[F:33])[O:21][N:20]=3)=[CH:23][C:24]=2[CH3:31])[N:6]=[CH:7][CH:2]=[CH:3][NH:4]1

Participants

4

Reactant 3

HCID 1049PyridineHCID 122159932-Chloropyrimidin-5-amineHCID 866114794-(5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methylbenzoyl chloride

Product 1

HCID 86654472N-(2-chloro-2-pyrimidinyl)-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole-3-yl]-2-methyl benzoic acid amide

Procedure

In a solution of 0.12 g of 5-amino-2-chloropyrimidine in 3 mL of pyridine, 0.36 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 was added at room temperature with stirring, and stirred at the same temperature for 18 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure, 30 mL of 3N hydrochloric acid was added in the residue, and extracted with ethyl acetate (30 mL×1). The organic phase was washed with water, and then dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (2:3) to obtain 0.24 g of the aimed product as white crystal.

Workup

  1. stirringstirred at the same temperature for 18 hours
  2. customAfter the completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure, 30 mL of 3N hydrochloric acid
  4. additionwas added in the residue
  5. extractionextracted with ethyl acetate (30 mL×1)
  6. washThe organic phase was washed with water
  7. dry with materialdried over saturated sodium chloride aqueous solution
  8. distillationanhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure
  9. customThe residue was purified with silica gel column chromatography that

Sources & evidence

ORD record
ord-ceec9f14533540859b08a0c232807e03
Source dataset
uspto-grants-2015_03
Patent number
US08987464B2

Reaction notes

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