Water → 4-Chloro-N-[5-chloro-2-(2-oxazol-2-yl-benzoyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide

HRID 419115Notes

Reaction equation

HRID 419115 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:34])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[O:30][CH:31]=[CH:32][N:33]=3)=[N:17][CH:18]=[C:19]([Cl:21])[CH:20]=2)COC)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:35]([F:38])([F:37])[F:36].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:34])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[O:30][CH:31]=[CH:32][N:33]=3)=[N:17][CH:18]=[C:19]([Cl:21])[CH:20]=2)(=[O:9])=[O:10])=[CH:4][C:3]=1[C:35]([F:37])([F:38])[F:36]

Participants

5

Reactant 2

HCID 962WaterHCID 579423584-Chloro-N-[5-chloro-2-(2-oxazol-2-yl-benzoyl)-Pyridin-3-yl]-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide

Product 1

HCID 579425684-Chloro-N-[5-chloro-2-(2-oxazol-2-yl-benzoyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamideYield 57.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-Chloro-N-[5-chloro-2-(2-oxazol-2-yl-benzoyl)-pyridin-3-yl]-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide (15 mg) in 2 mL of 4M HCl in dioxane and 1 mL of water was refluxed for 2 hours. After cooling to rt the mixture was concentrated, diluted with water and then sodium bicarbonate was added until pH was 6. The mixture was extracted with ethyl acetate, dried and concentrated. The residue was purified via flash column (35% ethyl acetate in hexane) to afford 8.0 mg of title compound as an off white solid. MS: (M+H)/z=542.3.

Workup

  1. concentrationwas concentrated
  2. additiondiluted with water
  3. additionsodium bicarbonate was added until pH was 6
  4. extractionThe mixture was extracted with ethyl acetate
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified via flash column (35% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-38ea76be367941df8c34c8c03e835272
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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