Isoxazole, 4-(chloromethyl)-3,5-dimethyl- → HCID 72194136, compound

HRID 594149Notes

Reaction equation

HRID 594149 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:12]2[N:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[F-].[K+].Cl[CH2:29][C:30]1[C:31]([CH3:36])=[N:32][O:33][C:34]=1[CH3:35]>C(#N)C>[CH3:36][C:31]1[C:30]([CH2:29][O:1][C:2]2[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:12]3[N:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][N:13]=3)(=[O:9])=[O:10])=[CH:4][CH:3]=2)=[C:34]([CH3:35])[O:33][N:32]=1

Participants

5

Reactant 3

HCID 88246Isoxazole, 4-(chloromethyl)-3,5-dimethyl-HCID 522689Potassium FluorideHCID 89876099HCID 89876099, compound

Product 1

HCID 72194136HCID 72194136, compoundYield 121.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a suspension of 4-hydroxy-N-(2-methylpropyl)-N-[4-(trifluoromethyl)-2-pyrimidinyl]benzenesulfonamide (31 mg, 0.083 mmol) and potassium fluoride on alumina (30 mg, 0.207 mmol) in acetonitrile (0.5 mL) stirred under nitrogen at room temperature was added a solution of 4-(chloromethyl)-3,5-dimethylisoxazole (12 mg, 0.083 mmol) in acetonitrile (0.5 mL). The reaction mixture was stirred at 20° C. for 16 hours. The reaction mixture was filtered to remove the potassium fluoride on alumina and the filtrate evaporated. The sample was purified by mass directed autoprep (TFA modifier). The solvent was evaporated under a stream of nitrogen and then freeze-dried from water/dioxane to give the title compound (49 mg). LCMS (2 min, formic) Rt 1.35 min, m/z (ES+) 485 (M+H).

Workup

  1. stirringThe reaction mixture was stirred at 20° C. for 16 hours
  2. filtrationThe reaction mixture was filtered
  3. customto remove the potassium fluoride on alumina
  4. customthe filtrate evaporated
  5. customThe sample was purified by mass
  6. customThe solvent was evaporated under a stream of nitrogen
  7. dry with materialfreeze-dried from water/dioxane

Sources & evidence

ORD record
ord-01c692ff06014ef69da4755a0879acda
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

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