Pyridine → HCID 11732410, compound

HRID 1584659Notes

Reaction equation

HRID 1584659 reaction equation
[C:1]1([C:7]2[NH:8][C:9](=[O:24])[N:10]([S:12]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[NH:20][CH2:19][CH2:18]4)(=[O:14])=[O:13])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[CH2:31]([O:33][C:34](Cl)=[O:35])[CH3:32]>ClCCl>[C:1]1([C:7]2[NH:8][C:9](=[O:24])[N:10]([S:12]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[N:20]([C:34]([O:33][CH2:31][CH3:32])=[O:35])[CH2:19][CH2:18]4)(=[O:14])=[O:13])[CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 11002343HCID 11002343, compound

Product 1

HCID 11732410HCID 11732410, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Phenyl-1-(indoline-5-sulfonyl)-2-imidazolone (150 mg, 0.44 mmol) prepared in Preparation 3 was dissolved in 10 ml of dichloromethane and then pyridine (39 μl, 0.484 mmol) and ethylchloroformate (46 μl, 0.484 mmol) were added thereto one after another. After the reaction mixture was stirred for one hour at room temperature, it was diluted with dichloromethane and washed twice with brine. The organic layer thus obtained was dried over anhydrous magnesium sulfate, concentrated to an oily state under reduced pressure, and then purified by silica gel column chromatography (eluent:dichloromethane/methanol=15/1, v/v) to afford 173 mg of the title compound as a white solid.

Workup

  1. washwashed twice with brine
  2. customThe organic layer thus obtained
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationconcentrated to an oily state under reduced pressure
  5. custompurified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-0065ecb56cfa45679d086db3243627a3
Source dataset
uspto-grants-1999_08
Patent number
US05932742

Reaction notes

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