Acetic Acid → HCID 57561071, compound

HRID 1724864Notes

Reaction equation

HRID 1724864 reaction equation
CO[C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:6][C:5]=1[NH2:20].[C:22](O)(=[O:24])[CH3:23].O.C[Si]([N-][Si](C)(C)C)(C)C.[K+]>O1CCOCC1.C1(C)C=CC=CC=1>[OH:21][C:3]1[C:4]2[C:5](=[CH:6][C:7]([C:10]3[C:15]([C:16]([F:17])([F:18])[F:19])=[CH:14][CH:13]=[CH:12][N:11]=3)=[CH:8][CH:9]=2)[NH:20][C:22](=[O:24])[CH:23]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 3251421Potassium bis(trimethylsilyl)amideHCID 46203234HCID 46203234, compound

Product 1

HCID 57561071HCID 57561071, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

Heat a solution of 2-amino-4-(3-trifluoromethyl-pyridin-2-yl)-benzoic acid methyl ester (296 mg, 1.0 mmol) and acetic acid (1 mL) in dioxane (2 mL) at 60° C. for 3 hours. Cool the mixture, add water (1 mL) and evaporate to dryness. Dissolve the solid in THF (4 mL) and add drop wise to a solution of potassium bis(trimethylsilyl)amide (600 mg, 3.0 mmol) in toluene (6 mL) at −78° C. Allow the reaction to return to room temperature overnight. Add water (10 mL) and extract with ethyl acetate. Acidify the aqueous layer with hydrochloric acid and collect the precipitate by filtration. Air-dry to give the title compound.

Workup

  1. temperatureCool the mixture
  2. customevaporate to dryness
  3. dissolutionDissolve the solid in THF (4 mL)
  4. customthe reaction
  5. extractionAdd water (10 mL) and extract with ethyl acetate
  6. customcollect the precipitate
  7. filtrationby filtration
  8. customAir-dry

Sources & evidence

ORD record
ord-fad920d4db394ebf97236c1ae9946896
Source dataset
uspto-grants-2009_02
Patent number
US07488740B2

Reaction notes

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