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6-(2-Oxooxazolidin-3-yl)nicotinic acid methyl ester → 3-{5-[4-(3,5,6-Trimethylpyridin-2-yl)piperazine-1-carbonyl]pyridin-2-yl}oxazolidin-2-one

HRID 1804313
Notes
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Reaction equation

HRID 1804313 reaction equation
CO[C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][O:12][C:11]2=[O:15])=[N:6][CH:5]=1.Cl.[CH3:18][C:19]1[C:20]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[N:21][C:22]([CH3:26])=[C:23]([CH3:25])[CH:24]=1>>[CH3:18][C:19]1[C:20]([N:27]2[CH2:28][CH2:29][N:30]([C:3]([C:4]3[CH:9]=[CH:8][C:7]([N:10]4[CH2:14][CH2:13][O:12][C:11]4=[O:15])=[N:6][CH:5]=3)=[O:16])[CH2:31][CH2:32]2)=[N:21][C:22]([CH3:26])=[C:23]([CH3:25])[CH:24]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 584844956-(2-Oxooxazolidin-3-yl)nicotinic acid methyl esterHCID 673810521-(3,5,6-Trimethylpyridin-2-yl)piperazine hydrochloride

Product 1

HCID 584845093-{5-[4-(3,5,6-Trimethylpyridin-2-yl)piperazine-1-carbonyl]pyridin-2-yl}oxazolidin-2-oneYield 21.4%

Procedure

By reaction and treatment in the same manner as in Example 63 and using 6-(2-oxooxazolidin-3-yl)nicotinic acid methyl ester (250 mg) described in Preparation Example 138 and 1-(3,5,6-trimethylpyridin-2-yl)piperazine hydrochloride (328 mg) described in Preparation Example 52 after neutralization and conversion to a free form, the title compound (95 mg) was obtained.

Workup

  • customBy reaction and treatment in the same manner as in Example 63
  • customdescribed in Preparation Example 52 after neutralization and conversion to a free form
  • Sources & evidence

    ORD record
    ord-991e4ba0dd4146118d756ce55efd46ae
    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