Ammonium Chloride → HCID 67777563, compound

HRID 1026308Notes

Reaction equation

HRID 1026308 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[C:13]([CH:14]=2)=[N:12][N:11]([C:15]2[CH:31]=[CH:30][C:18]([O:19]S(C(F)(F)C(OC)=O)(=O)=O)=[CH:17][CH:16]=2)[C:10]=3[C:32]([F:35])([F:34])[F:33])[CH2:3][CH2:2]1.CO.C[O-].[Na+].[Cl-].[NH4+]>CO>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[C:13]([CH:14]=2)=[N:12][N:11]([C:15]2[CH:31]=[CH:30][C:18]([OH:19])=[CH:17][CH:16]=2)[C:10]=3[C:32]([F:34])([F:35])[F:33])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23694274Sodium methanolate methanolHCID 86666302HCID 86666302, compound

Product 1

HCID 67777563HCID 67777563, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl ({4-[6-(cyclopropylmethoxy)-3-(trifluoromethyl)-2H-indazol-2-yl]phenoxy}sulfonyl)(difluoro)acetate (365 mg) in methanol (4 mL) was added dropwise 27% sodium methoxide methanol solution (1 mL) at room temperature, and the mixture was stirred for 3 hr. The reaction mixture was neutralized with saturated aqueous ammonium chloride solution, and extracted twice with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as a colorless powder (179 mg).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-725d52a96a8f453aa520032b4cc3a4b6
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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