Water → HCID 86654458, compound

HRID 1187965Notes

Reaction equation

HRID 1187965 reaction equation
[Br: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.[C:42](Cl)(=[O:46])[CH:43]([CH3:45])[CH3:44].O>CN(C)C1C=CN=CC=1.O1CCCC1>[Br:1][C:2]1[CH:7]=[N:6][C:5]([N:8]([C:42](=[O:46])[CH:43]([CH3:45])[CH3:44])[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

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 86654457HCID 86654457, compound

Product 1

HCID 86654458HCID 86654458, compoundYield 51.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a solution of 1.5 g of N-(5-bromo-2-pyrimidinyl)-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl benzoic acid amide, 0.42 g of triethylamine and 0.03 g of 4-(dimethylamino)pyridine in 50 mL of tetrahydrofuran, 0.42 g of isobutyryl chloride was added at room temperature with stirring and stirred at the same temperature for 18 hours. After the completion of the reaction, 50 mL of water was added in the reaction mixture, extracted with ethyl acetate (80 mL×1), 5 g of silica gel was added in the organic phase, stirred and filtered off, and then the solvent was distilled off under reduced pressure. The residue was subjected to crystallization from diethyl ether and hexane to obtain 0.87 g of the aimed product as white crystal.

Workup

  1. stirringstirred at the same temperature for 18 hours
  2. additionwas added in the reaction mixture
  3. extractionextracted with ethyl acetate (80 mL×1), 5 g of silica gel
  4. additionwas added in the organic phase
  5. stirringstirred
  6. filtrationfiltered off
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was subjected to crystallization from diethyl ether and hexane

Sources & evidence

ORD record
ord-f88a3639a10d45dab1fc85052d743b20
Source dataset
uspto-grants-2014_03
Patent number
US08673951B2

Reaction notes

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