2,5-Pyrrolidinedione, 3-methylene-1-phenyl- → 3-({4-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperazinyl}methyl)-1-phenylazolidine-2,5-dione

HRID 271246Notes

Reaction equation

HRID 271246 reaction equation
[CH2:1]=[C:2]1[CH2:6][C:5](=[O:7])[N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]1=[O:14].[CH3:15][C:16]1[S:17][C:18]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH:27]([OH:35])[CH2:28][N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)=[CH:21][C:19]=2[N:20]=1>CC(O)=O>[OH:35][C@@H:27]([CH2:26][O:25][C:22]1[CH:23]=[CH:24][C:18]2[S:17][C:16]([CH3:15])=[N:20][C:19]=2[CH:21]=1)[CH2:28][N:29]1[CH2:30][CH2:31][N:32]([CH2:1][CH:2]2[CH2:6][C:5](=[O:7])[N:4]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:3]2=[O:14])[CH2:33][CH2:34]1

Participants

4

Reactant 2

HCID 131082272,5-Pyrrolidinedione, 3-methylene-1-phenyl-HCID 219116911-(2-Methylbenzothiazol-5-yloxy)-3-piperazin-1-ylpropan-2-ol

Product 1

HCID 112948703-({4-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperazinyl}methyl)-1-phenylazolidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-methylene-1-phenylazolidine-2,5-dione (250 mg, 1.33 mmol) and 1-(2-methylbenzothiazol-5-yloxy)-3-piperazin-1-ylpropan-2-ol (415 mg, 1.35 mmol) in AcOH (10 mL, glacial) was stirred 14 hours at 50° C. Concentrated in the Savant™ and residue taken up in EtOAc and washed with NaHCO3 (sat. aq. soln.), H2O and brine, dried over MgSO4, filtered and concentrated. Purification via flash column chromatography (gradient 5 to 10% MeOH/EtOAc) afforded 3-({4-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperazinyl}methyl)-1-phenylazolidine-2,5-dione.

Workup

  1. concentrationConcentrated in the Savant™ and residue
  2. washwashed with NaHCO3 (sat. aq. soln.), H2O and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification via flash column chromatography (gradient 5 to 10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-2fef8e5bf9a74113a3f628c85f1eabbc
Source dataset
uspto-grants-2008_11
Patent number
US07452889B2

Reaction notes

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