p-Toluenesulfonic acid → HCID 136342062, compound

HRID 269518Notes

Reaction equation

HRID 269518 reaction equation
C[N:2](C)[CH:3]=[C:4]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[F:24])[C:5]([C:7]1[C:15]2[CH:14]=[CH:13][N:12]([CH3:16])[C:11](=[O:17])[C:10]=2[NH:9][CH:8]=1)=[O:6].C(=O)([O-])O.[Na+].Cl.NO.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCCC1.C(OCC)(=O)C>[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:4]1[CH:3]=[N:2][O:6][C:5]=1[C:7]1[C:15]2[CH:14]=[CH:13][N:12]([CH3:16])[C:11](=[O:17])[C:10]=2[NH:9][CH:8]=1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 69207138HCID 69207138, compound

Product 1

HCID 136342062HCID 136342062, compoundYield 27.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To 3-[3-Dimethylamino-2-(2-fluoro-phenyl)-acryloyl]-6-methyl-1, 6-dihydro-pyrrolo[2,3-c]pyridin-7-one (79 mg, 0.22 mmol) in tetrahydrofuran (20 mL) was added sodium hydrogen carbonate (19 mg, 0.0.27 mmol) and hydroxylamine Hydrochloride (23 mg, 0.27 mmol) and the mixture was heated to 80C. After 5 hr p-toluenesulfonic acid (catalytic amount) was added and the reaction mixture was heated for an additional 1 hr. The solution was cooled, diluted with ethyl acetate, washed with brine, dried (Na2SO4). Concentration gave an amber oil. Preparative reverse phase chromatography afforded 3-[4-(2-Fluoro-phenyl)-isoxazol-5-yl]-6-methyl-1,6-dihydro-pyrrolo[2,3-c]pyridin-7-one (18.6 mg, 25% yield).

Workup

  1. temperaturethe reaction mixture was heated for an additional 1 hr
  2. temperatureThe solution was cooled
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationConcentration
  6. customgave an amber oil

Sources & evidence

ORD record
ord-3196eaafec9e430299b18a3feff028fc
Source dataset
uspto-grants-2008_11
Patent number
US07446199B2

Reaction notes

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