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Acetic Acid → HCID 25023595, compound

HRID 2076359
Notes
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Reaction equation

HRID 2076359 reaction equation
[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13]3[C:19](=O)[C:18]([CH2:26][CH2:27][F:28])([CH2:21][CH2:22][C:23](=[O:25])[CH3:24])[CH2:17][C:14]=32)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1CCCC1.C(O)(=O)C>C1(C)C=CC=CC=1.CCCCCCC.ClCCl>[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13]3[C:19]4[C:18]([CH2:26][CH2:27][F:28])([CH2:21][CH2:22][C:23](=[O:25])[CH:24]=4)[CH2:17][C:14]=32)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 59397215HCID 59397215, compound

Product 1

HCID 25023595HCID 25023595, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 21907733Dichloromethane heptaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-benzyl-7-(2-fluoroethyl)-7-(3-oxobutyl)-7,8-dihydrocyclopenta[e]indazol-6(2H)-one (10.8 g, 28.6 mmol) in 300 mL of toluene were added pyrrolidine (2.4 mL, 28.6 mmol) and acetic acid (1.64 mL, 28.6 mmol) and the solution was heated at 90° C. under nitrogen. After 15 hours, the solution was cooled to room temperature and partitioned between EtOAc and water. The organic phase was washed with 5% aqueous NaHCO3 and brine and dried over MgSO4. Evaporation of the solvent under vacuum gave a brown oil which was purified by chromatography on silica gel (1:2 to 1:1 EtOAc/hexanes) to give a sticky orange solid. The solid was dissolved in heptane-dichloromethane and then most of the dichloromethane was evaporated under reduced pressure. The resulting precipitated solid was isolated by filtration to give 2-benzyl-9a-(2-fluoroethyl)-8,9,9a,10-tetrahydroindeno[2,1-e]indazol-7(2H) -one.

Workup

  1. temperaturethe solution was cooled to room temperature
  2. custompartitioned between EtOAc and water
  3. washThe organic phase was washed with 5% aqueous NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. customEvaporation of the solvent under vacuum
  6. customgave a brown oil which
  7. customwas purified by chromatography on silica gel (1:2 to 1:1 EtOAc/hexanes)
  8. customto give a sticky orange solid
  9. custommost of the dichloromethane was evaporated under reduced pressure
  10. customThe resulting precipitated solid
  11. customwas isolated by filtration

Sources & evidence

ORD record
ord-a76086e7fe90420a856cff39c463235a
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07923568B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes