Hydrochloric Acid → HCID 25130780, compound

HRID 2262531Notes

Reaction equation

HRID 2262531 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:8][O:9][C:10]=2[C:11]([F:14])([F:13])[F:12])[N:3]=[CH:2]1.[CH3:21][C:22]([C:24]1[CH:29]=[CH:28][C:27](F)=[CH:26][CH:25]=1)=[O:23].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C>[C:15]1([C:7]2[C:6]([C:4]3[N:3]=[CH:2][N:1]([C:27]4[CH:28]=[CH:29][C:24]([C:22](=[O:23])[CH3:21])=[CH:25][CH:26]=4)[CH:5]=3)=[C:10]([C:11]([F:14])([F:12])[F:13])[O:9][N:8]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 98284'-FluoroacetophenoneHCID 11430Potassium CarbonateHCID 178506308HCID 178506308, compound

Product 1

HCID 25130780HCID 25130780, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-(1H-imidazol-4-yl)-3-phenyl-5-trifluoromethyl-isoxazole (70 mg, 0.25 mmol) in DMF (2.5 mL) was added 4-fluoroacetophenone (35 mg, 0.25 mmol) and potassium carbonate (69.1 mg, 0.5 mmol) and the resulting mixture heated at 120° C. overnight. The resulting mixture was then poured into HCl (1 N, 200 mL) and extracted with ethyl acetate which was then washed with brine, dried over sodium sulphate and evaporated. Purification by preparative HPLC on reversed phase eluting with an acetonitrile/water [0.1% aq NH3 (25%)] gradient afforded the title compound (25 mg, 25%) which was obtained as a white solid. MS: m/e=398.1 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate which
  2. washwas then washed with brine
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customPurification by preparative HPLC on reversed phase
  6. washeluting with an acetonitrile/water [0.1% aq NH3 (25%)] gradient

Sources & evidence

ORD record
ord-8a5cc849ce0841709020e807826c9723
Source dataset
uspto-grants-2010_12
Patent number
US07851469B2

Reaction notes

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