Thionyl Chloride → HCID 12680375, compound

HRID 861333Notes

Reaction equation

HRID 861333 reaction equation
[F-].[Cs+].[CH2:3]([NH:6][C:7](=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:4][CH3:5].S(Cl)([Cl:17])=O.C([O-])(O)=O.[Na+]>O.ClCCl>[CH2:3]([N:6]=[C:7]([Cl:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 25354Benzamide, N-propyl-HCID 25953Cesium fluorideHCID 516892Sodium Bicarbonate

Product 1

HCID 12680375HCID 12680375, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

(5RS,6SR,7SR)-6-Tert-butoxycarbonyl-7-(2-benzyloxy-4-methoxyphenyl)-5-(3,4-methylenedioxyphenyl)cyclopenteno[1,2-b]pyridine N-oxide(224 mg, 0.395 mmol) and CsF(1.82 g) were dried under reduced pressure. To the mixture were added dichloromethane(4.0 ml) under nitrogen atmosphere and N-propylbenzimidoyl chloride(210 mg) which was prepared from benzoic acid N-propylamide and thionyl chloride. The solution was stirred vigorously under heating at reflux, treated with an aqueous saturated solution of NaHCO3 and water, stirred at room temperature to make the solution homogeneous and extracted with dichloromethane. The organic layer was washed with brine and dried over MgSO4. After removal of the solvent the residue was purified by MPL(E. Merck Kieselgel 60 lobar column/dichloromethane:acetone=100:1 to 50:1 to 30:1) to give (5RS,6SR,7SR)-6-tert-butoxycarbonyl-7-(2-benzyloxy-4-methoxyphenyl)-2-[(N-benzoyl)propylamino]-5-(3,4-methylenedioxyphenyl)cyclopenteno[1,2-b]pyridine(138 mg).

Workup

  1. temperatureunder heating
  2. temperatureat reflux
  3. stirringstirred at room temperature
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. customAfter removal of the solvent the residue
  8. customwas purified by MPL(E

Sources & evidence

ORD record
ord-323d926f6cd044acb42206f5862dd055
Source dataset
uspto-grants-1998_02
Patent number
US05714479

Reaction notes

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