Water → HCID 56598750, compound

HRID 2283609Notes

Reaction equation

HRID 2283609 reaction equation
[OH-].[K+].O.FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[Cl:18][C:19]1[C:20]([O:35][C:36]2[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[C:39]([F:46])=[CH:38][C:37]=2[C:47]2[CH:52]=[CH:51][N:50]=[N:49][CH:48]=2)=[CH:21][C:22]([F:34])=[C:23]([S:25]([NH:28][C:29]2[N:30]=[CH:31][S:32][CH:33]=2)(=[O:27])=[O:26])[CH:24]=1>C(OCC)C>[Cl:18][C:19]1[C:20]([O:35][C:36]2[CH:41]=[C:40]([C:42]([F:43])([F:45])[F:44])[C:39]([F:46])=[CH:38][C:37]=2[C:47]2[CH:52]=[CH:51][N:50]=[N:49][CH:48]=2)=[CH:21][C:22]([F:34])=[C:23]([S:25]([NH:28][C:29]2[N:30]=[CH:31][S:32][CH:33]=2)(=[O:27])=[O:26])[CH:24]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 86682360HCID 86682360, compound

Product 1

HCID 56598750HCID 56598750, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 1.0 M potassium hydroxide in water (65 mL, 65 mmol) was added to 5-chloro-2-fluoro-4-[4-fluoro-2-pyridazin-4-yl-5-(trifluoromethyl)phenoxy]-N-1,3-thiazol-4-ylbenzenesulfonamide bis(trifluoroacetate) (2.37 g, 3.05 mmol). The mixture was stirred at ambient temperature. Diethyl ether was added and the layers separated. The aqueous layer was acidified to pH 4 with 10 wt % citric acid in water. A precipitate developed so the mixture was sonicated then stirred for 45 minutes at ambient temperature. The aqueous layer was extracted with ethyl acetate (4×50 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, treated with charcoal, filtered through diatomaceous earth, and concentrated in vacuo. The residue was taken up in acetone and ether and concentrated in vacuo to give 5-chloro-2-fluoro-4-[4-fluoro-2-pyridazin-4-yl-5-(trifluoromethyl)phenoxy]-N-1,3-thiazol-4-ylbenzenesulfonamide as a solid which was used without further purification.

Workup

  1. customthe layers separated
  2. customwas sonicated
  3. stirringthen stirred for 45 minutes at ambient temperature
  4. extractionThe aqueous layer was extracted with ethyl acetate (4×50 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. additiontreated with charcoal
  8. filtrationfiltered through diatomaceous earth
  9. concentrationconcentrated in vacuo
  10. concentrationether and concentrated in vacuo

Sources & evidence

ORD record
ord-5b1f353d72434393834bba5836820763
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

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