HCID 18936646, compound → HCID 57245668, compound

HRID 357197Notes

Reaction equation

HRID 357197 reaction equation
O[CH:2]([CH:8]1[O:12][C:11](=[O:13])[N:10]([CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]2[C:20]3[N:21]([CH:25]=[CH:26][N:27]=3)[CH:22]=[CH:23][CH:24]=2)[C:9]1=[O:28])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]>N1C=CC=CC=1.C(OC(=O)C)(=O)C.ClCCl>[CH:2](=[C:8]1[O:12][C:11](=[O:13])[N:10]([CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]2[C:20]3[N:21]([CH:25]=[CH:26][N:27]=3)[CH:22]=[CH:23][CH:24]=2)[C:9]1=[O:28])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 1

HCID 18936646HCID 18936646, compound

Product 1

HCID 57245668HCID 57245668, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of 386 mg (0.99 mmol) of 5-(1-hydroxyhexyl)-3-[4-(imidazo[1,2-a]pyridin-8-yloxy)butyl]oxazolidine-2,4-dione in 8 ml of pyridine, 4 ml of acetic anhydride was added, followed by stirring at room temperature for 2 hours and then at 90° C. for 21 hours. The mixture was dissolved in dichloromethane, washed with saturated aqueous sodium hydrogen carbonate and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, ethyl acetate/hexane=4/1→ethyl acetate) to yield 79.2 mg (22%, yellow oily substance) of the desired product.

Workup

  1. waitat 90° C. for 21 hours
  2. washwashed with saturated aqueous sodium hydrogen carbonate
  3. customdried
  4. distillationafter which the solvent was distilled off
  5. customThe residue was purified by column chromatography (eluent, ethyl acetate/hexane=4/1→ethyl acetate)

Sources & evidence

ORD record
ord-3c28407000b04d24b05767b559429469
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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