Acetic Acid → HCID 24739204, compound

HRID 889498Notes

Reaction equation

HRID 889498 reaction equation
[CH2:1]([O:3][C:4]1[C:12]2[CH2:11][N:10]([C:13]3[C:18]([F:19])=[CH:17][C:16]([CH2:20][C:21]([O:23]CC)=[O:22])=[CH:15][C:14]=3[F:26])[C:9](=[O:27])[C:8]=2[C:7]([O:28][CH2:29][CH3:30])=[C:6]2[CH:31]=[CH:32][CH:33]=[CH:34][C:5]=12)[CH3:2].C(O)(=O)C.Cl>O>[CH2:1]([O:3][C:4]1[C:12]2[CH2:11][N:10]([C:13]3[C:18]([F:19])=[CH:17][C:16]([CH2:20][C:21]([OH:23])=[O:22])=[CH:15][C:14]=3[F:26])[C:9](=[O:27])[C:8]=2[C:7]([O:28][CH2:29][CH3:30])=[C:6]2[CH:31]=[CH:32][CH:33]=[CH:34][C:5]=12)[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 58399557HCID 58399557, compound

Product 1

HCID 24739204HCID 24739204, compoundYield 41.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To ethyl {4-[4,9-bis(ethyloxy)-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]-3,5-difluorophenyl}acetate (0.045 g, 0.096 mml) was added acetic acid (3 ml) and 2N hydrochloric acid (3 ml). This was heated to 100° C. for 1 hour. Heating was stopped and the reaction was cooled to room temperature, water added and the resulting yellow solid collected by filtration and dried in the vac oven. This was purified by MDAP (Shallow gradient). The clean fraction was evaporated down to give the title compound as a clear glass (0.018 g, 0.04 mmol) LC/MS: Rt=3.16, [MH]+ 442.

Workup

  1. temperatureHeating
  2. temperaturethe reaction was cooled to room temperature
  3. filtrationthe resulting yellow solid collected by filtration
  4. customdried in the vac oven
  5. customThis was purified by MDAP (Shallow gradient)
  6. customThe clean fraction was evaporated down

Sources & evidence

ORD record
ord-727115a452ad4322961567008a19bdc8
Source dataset
uspto-grants-2012_08
Patent number
US08252833B2

Reaction notes

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