1-[6-(Benzyloxy)pyridin-3-YL]ethanone → 5-(4-{2-[1-(2-Benzyloxy-5-pyridyl)ethylideneaminooxy]ethoxy}benzyl)thiazolidine-2,4-dione

HRID 1741329Notes

Reaction equation

HRID 1741329 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:8][CH:9]=1)(=O)[CH3:2].Cl.[NH2:19][O:20][CH2:21][CH2:22][O:23][C:24]1[CH:37]=[CH:36][C:27]([CH2:28][CH:29]2[S:33][C:32](=[O:34])[NH:31][C:30]2=[O:35])=[CH:26][CH:25]=1>>[CH2:11]([O:10][C:7]1[CH:6]=[CH:5][C:4]([C:1](=[N:19][O:20][CH2:21][CH2:22][O:23][C:24]2[CH:25]=[CH:26][C:27]([CH2:28][CH:29]3[S:33][C:32](=[O:34])[NH:31][C:30]3=[O:35])=[CH:36][CH:37]=2)[CH3:2])=[CH:9][N:8]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 218339271-[6-(Benzyloxy)pyridin-3-YL]ethanoneHCID 218339655-(4-[2-Aminooxyethoxy)benzyl]thiazolidine-2,4-dione hydrochloride

Product 1

HCID 738479805-(4-{2-[1-(2-Benzyloxy-5-pyridyl)ethylideneaminooxy]ethoxy}benzyl)thiazolidine-2,4-dioneYield 78%

Procedure

Following a procedure similar to that described in Example 40(f), 130 mg of 5-acetyl-2-benzyloxypyridine were reacted with 182 mg of 5-[4-(2-aminooxyethoxy)-benzyl]thiazolidine-2,4-dione hydrochloride [prepared as described in Example 40(e)]. The reaction mixture was concentrated by evaporation under reduced pressure, and the resulting residue was extracted with ethyl acetate. The extract was washed with water and the solvent was removed by distillation under reduced pressure, to give 219 mg of the title compound, melting at 160-161° C.

Workup

  1. concentrationThe reaction mixture was concentrated by evaporation under reduced pressure
  2. extractionthe resulting residue was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-cdaa34589ada49e3abe2745fd1a9ad28
Source dataset
uspto-grants-1999_10
Patent number
US05972959

Reaction notes

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