Water → HCID 57942443, compound

HRID 419043Notes

Reaction equation

HRID 419043 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:35])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N:29]([S:31]([CH3:34])(=[O:33])=[O:32])[CH3:30])=[N:17][CH:18]=[C:19]([Cl:21])[CH:20]=2)COC)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:36]([F:39])([F:38])[F:37].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:35])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N:29]([S:31]([CH3:34])(=[O:33])=[O:32])[CH3:30])=[N:17][CH:18]=[C:19]([Cl:21])[CH:20]=2)(=[O:9])=[O:10])=[CH:4][C:3]=1[C:36]([F:39])([F:37])[F:38]

Participants

5

Reactant 2

HCID 962WaterHCID 57942298HCID 57942298, compound

Product 1

HCID 57942443HCID 57942443, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture 4-chloro-N-{5-chloro-2-[2-(methanesulfonyl-methyl-amino)-benzoyl]-pyridin-3-yl}-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide (30 mg crude) in 4 M HCl in dioxane (12 mL) and water (4 mL) were heated at 100° C. for 18 h. The reaction mixture was concentrated to dryness under reduced pressure and subsequently neutralized aqueous NaHCO3 to pH to 5-6. The aqueous layer was extracted with EtOAc, the combined extracts were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by preparative HPLC (20→80% gradient of MeCN-water) to provide 4-chloro-N-{5-chloro-2-[2-(methanesulfonyl-methyl-amino)-benzoyl]-pyridin-3-yl}-3-trifluoromethyl-benzenesulfonamide as a solid. MS m/z: 582.0 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure and subsequently neutralized aqueous NaHCO3
  2. extractionThe aqueous layer was extracted with EtOAc
  3. dry with materialthe combined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by preparative HPLC (20→80% gradient of MeCN-water)

Sources & evidence

ORD record
ord-d7cce9bfaa9f4b228a5e8ab57d8eea48
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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