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(R)-4-(4-ethyl-2-oxooxazolidin-3-yl)benzoic acid → (R)-3-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-4-ethyloxazolidin-2-one

HRID 1804196
Notes
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Reaction equation

HRID 1804196 reaction equation
[CH2:1]([C@@H:3]1[CH2:7][O:6][C:5](=[O:8])[N:4]1[C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)[CH3:2].Cl.[CH3:19][C:20]1[C:21]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[N:22][CH:23]=[C:24]([CH3:26])[CH:25]=1>>[CH3:19][C:20]1[C:21]([N:27]2[CH2:28][CH2:29][N:30]([C:13]([C:12]3[CH:11]=[CH:10][C:9]([N:4]4[C@H:3]([CH2:1][CH3:2])[CH2:7][O:6][C:5]4=[O:8])=[CH:17][CH:16]=3)=[O:15])[CH2:31][CH2:32]2)=[N:22][CH:23]=[C:24]([CH3:26])[CH:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 58484770(R)-4-(4-ethyl-2-oxooxazolidin-3-yl)benzoic acidHCID 673813791-(3,5-Dimethylpyridin-2-yl)piperazine hydrochloride

Product 1

HCID 67381186(R)-3-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-4-ethyloxazolidin-2-oneYield 38.2%

Procedure

By reaction and treatment in the same manner as in Example 49 and using (R)-4-(4-ethyl-2-oxooxazolidin-3-yl)benzoic acid (470 mg) described in Preparation Example 78 and 1-(3,5-dimethylpyridin-2-yl)piperazine hydrochloride (455 mg) described in Preparation Example 64, the title compound (312 mg) was obtained.

Workup

  1. custom
By reaction and treatment in the same manner as in Example 49
  • customdescribed in Preparation Example 64
  • Sources & evidence

    ORD record
    ord-6a092a07f60540d8b2d45e8a32ae309e
    Source dataset
    uspto-grants-2013_01
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US08354401B2

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes