Water → 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-[1-(2-pyridyl)cyclopropyl] benzamide

HRID 1642751Notes

Reaction equation

HRID 1642751 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:27])([F:26])[F:25])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]1([NH2:37])[CH2:36][CH2:35]1.O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:25])([F:27])[F:26])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH:37][C:34]4([C:29]5[CH:30]=[CH:31][CH:32]=[CH:33][N:28]=5)[CH2:36][CH2:35]4)=[O:19])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 111054091-(Pyridin-2-yl)cyclopropanamineHCID 866114794-(5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methylbenzoyl chloride

Product 1

HCID 667564624-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-[1-(2-pyridyl)cyclopropyl] benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a solution of 0.50 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzoyl chloride in 10 mL of dichloromethane, 0.20 g of 1-(2-pyridyl)cyclopropylamine was dropped while stirring and ice-cooling the solution and after the completion of the dropping, the stirring was continued at room temperature for 2 hours. After the completion of the reaction, the reaction mixture was poured into 20 mL of water and extracted with ethyl acetate (20 mL×2). The organic phase was cleaned with water (10 mL×1) and then was dehydrated and dried with saturated brine and over anhydrous sodium sulfate, respectively, in this order, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1:1) to obtain 0.16 g of the objective substance as a yellow resin-state substance.

Workup

  1. temperatureice-cooling the solution
  2. customAfter the completion of the reaction
  3. extractionextracted with ethyl acetate (20 mL×2)
  4. dry with materialdried with saturated brine and over anhydrous sodium sulfate
  5. distillationrespectively, in this order, and the solvent was distilled off under reduced pressure
  6. customThe resultant residue was purified by silica gel column chromatography
  7. washeluting with ethyl acetate-hexane (1:1)
  8. customto obtain 0.16 g of the objective substance as a yellow resin-state substance

Sources & evidence

ORD record
ord-b13eb500cb784f9a857abb601b982a11
Source dataset
uspto-grants-2012_02
Patent number
US08119671B2

Reaction notes

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