Water → HCID 57942309, compound

HRID 419108Notes

Reaction equation

HRID 419108 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:15]2[C:16]([C:22](=[O:30])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:29])=[N:17][CH:18]=[C:19]([CH3:21])[CH:20]=2)COC)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:31]([F:34])([F:33])[F:32].O>Cl.O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:15]2[C:16]([C:22](=[O:30])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:29])=[N:17][CH:18]=[C:19]([CH3:21])[CH:20]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:31]([F:32])([F:34])[F:33]

Participants

5

Reactant 2

HCID 962WaterHCID 57942131HCID 57942131, compound

Product 1

HCID 57942309HCID 57942309, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-chloro-N-[2-(2-chloro-benzoyl)-5-methyl-pyridin-3-yl]-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide (260 mg, 0.49 mmol) in 4M HCl in dioxane (5 mL) and water (1 mL) was refluxed for 3 h. Reaction mixture was cooled to room temperature, evaporated to dryness and treated with saturated aqueous NaHCO3 solution till pH 7-8. The mixture was extracted with EtOAc (2×25 mL), dried (anhydrous Na2SO4) and concentrated. The obtained residue was purified by flash chromatography (SiO2, 70% EtOAc-hexanes) to afford 4-chloro-N-[2-(2-chloro-benzoyl)-5-methyl-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide (106 mg) as a white solid (after lyophilization) in 45% yield. ESMS m/z (relative intensity): 489 (M+H)+ (100).

Workup

  1. customReaction mixture
  2. customevaporated to dryness
  3. additiontreated with saturated aqueous NaHCO3 solution till pH 7-8
  4. extractionThe mixture was extracted with EtOAc (2×25 mL)
  5. dry with materialdried (anhydrous Na2SO4)
  6. concentrationconcentrated
  7. customThe obtained residue was purified by flash chromatography (SiO2, 70% EtOAc-hexanes)

Sources & evidence

ORD record
ord-4af7f7def2b042edaf1998a7ad25f0e1
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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