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

HRID 552632Notes

Reaction equation

HRID 552632 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([NH:8][C:9](=[O:34])[C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH2:20][C:19]([C:25]4[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=4)([C:21]([F:24])([F:23])[F:22])[O:18][N:17]=3)=[CH:12][C:11]=2[CH3:33])=[N:6][CH:7]=1.C(N(CC)CC)C.[CH3:42][O:43][CH2:44][C:45](Cl)=[O:46]>CN(C)C1C=CN=CC=1.O1CCCC1>[Cl:1][C:2]1[CH:7]=[N:6][C:5]([N:8]([C:45](=[O:46])[CH2:44][O:43][CH3:42])[C:9](=[O:34])[C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH2:20][C:19]([C:25]4[CH:26]=[C:27]([Cl:32])[CH:28]=[C:29]([Cl:31])[CH:30]=4)([C:21]([F:23])([F:24])[F:22])[O:18][N:17]=3)=[CH:12][C:11]=2[CH3:33])=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 86654456N-(5-chloro-2-pyrimidinyl)-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl benzoic acid amide

Product 1

HCID 25216764N-(5-Chloro-2-pyrimidinyl)-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole-3-yl]-N-methoxyacetyl-2-methyl benzoic acid amideYield 71.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a solution of 0.27 g of N-(5-chloro-2-pyrimidinyl)-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole-3-yl]-2-methyl benzoic acid amide synthesized in Step 1 of Synthetic Example 11, 0.08 g of triethylamine and a catalytic amount of 4-(dimethylamino)pyridine in 5 mL of tetrahydrofuran, 0.08 g of methoxyacetyl chloride was added at room temperature with stirring, and stirred at the same temperature for 0.5 hour. After the completion of the reaction, the solvent was distilled off under reduced pressure, the residue was passed through short-pass silica gel column that was eluated with ethyl acetate, and thereby insoluble material was removed. The solvent was distilled off under reduced pressure, and purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (3:7) to obtain 0.22 g of the aimed product as colorless resinous substance.

Workup

  1. stirringstirred at the same temperature for 0.5 hour
  2. customAfter the completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. custominsoluble material was removed
  5. distillationThe solvent was distilled off under reduced pressure
  6. custompurified with silica gel column chromatography that

Sources & evidence

ORD record
ord-91aca0864906407793389e141a8a2389
Source dataset
uspto-grants-2011_05
Patent number
US07951828B1

Reaction notes

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