Triethylamine → HCID 86631569, compound

HRID 885819Notes

Reaction equation

HRID 885819 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:13][C:12]([C:18]3[CH:23]=[C:22]([Br:24])[C:21]([F:25])=[C:20]([Br:26])[CH:19]=3)([C:14]([F:17])([F:16])[F:15])[O:11][N:10]=2)=[CH:5][C:4]=1[Cl:27].C(N(CC)CC)C.[C:35](Cl)(=[O:39])[CH2:36][CH2:37][CH3:38]>ClCCl.C(Cl)(Cl)Cl>[C:35]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:13][C:12]([C:18]3[CH:23]=[C:22]([Br:24])[C:21]([F:25])=[C:20]([Br:26])[CH:19]=3)([C:14]([F:17])([F:16])[F:15])[O:11][N:10]=2)=[CH:5][C:4]=1[Cl:27])(=[O:39])[CH2:36][CH2:37][CH3:38]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 86631568HCID 86631568, compound

Product 1

HCID 86631569HCID 86631569, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-aminomethyl-3-chlorophenyl)-5-(3,5-dibromo-4-fluorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole (70.0 mg) and triethylamine (15.0 mg) in dichloromethane (2 mL) was added butyryl chloride (15.4 mg) at 5° C. The reaction mixture was then stirred at room temperature for 1 hour. The resulting mixture was diluted with chloroform (2 mL) and washed with saturated aqueous sodium hydrogencarbonate solution (3 mL) and brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to provide a residue. The residue was purified by liquid chromatography (medium pressure collection apparatus: Purif-α2 manufactured by Moritex Corporation) eluted with ethyl acetate-hexane (1:10) to afford the title compound as a colorless resin (42.0 mg).

Workup

  1. washwashed with saturated aqueous sodium hydrogencarbonate solution (3 mL) and brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto provide a residue
  5. customThe residue was purified by liquid chromatography (medium pressure collection apparatus: Purif-α2 manufactured by Moritex Corporation)
  6. washeluted with ethyl acetate-hexane (1:10)

Sources & evidence

ORD record
ord-08e331060ab64a69be1762ff22538c5d
Source dataset
uspto-grants-2012_08
Patent number
US08242283B2

Reaction notes

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