Hydrochloric Acid → HCID 22713809, compound

HRID 352161Notes

Reaction equation

HRID 352161 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([OH:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O.Cl.C(N([CH2:20][CH3:21])CC)C.[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=1[C:30]1[C:34]([C:35](Cl)=[O:36])=[C:33]([CH3:38])[O:32]N=1.[CH2:39](O)C>ClCCl.O=[Pt]=O.C(Cl)(Cl)Cl>[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=1[C:30]1[C:34]([C:35]([NH:1][CH:4]2[CH2:9][CH2:8][CH2:7][CH:6]([CH2:10][C:11]([O:13][CH2:20][CH3:21])=[O:12])[CH2:5]2)=[O:36])=[C:33]([CH3:38])[O:32][CH:39]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 8471TriethylamineHCID 158763-Nitrophenylacetic acidHCID 27365813-(2-Chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonyl chloride

Product 1

HCID 22713809HCID 22713809, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-nitrophenylacetic acid, 1.0 g (5.5 mmol) in 90 mL of ethanol was added 1.0 g of PtO2 and 2 mL of 5N HCl. The mixture was hydrogenated overnight at 60° C. and 60 psi, filtered through celite and concentrated to dryness. To a solution of the residue in 15 mL of dichloromethane was added 3.0 mL (21.6 mmol) of triethylamine and 2.0 g (7.2 mmol) of 3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonyl chloride. The solution was stirred overnight at ambient temperature. Chloroform was added and the solution was washed with 0.5N HCl, saturated sodium bicarbonate, brine, dried over sodium sulfate, filtered and concentrated to dryness. The residue was chromatographed on silica gel using 5% acetone/dichloromethane as eluent to yield 2.0 g (66%) of the desired mixture of isomers as a white solid. 1H—NMR is consistent with structure. MS (ion spray) 423.2 (M+1).

Workup

  1. filtration60 psi, filtered through celite and
  2. concentrationconcentrated to dryness
  3. washthe solution was washed with 0.5N HCl, saturated sodium bicarbonate, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was chromatographed on silica gel using 5% acetone/dichloromethane as eluent

Sources & evidence

ORD record
ord-b6a56ff5c9734fa4af6ccd79d0ea1578
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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