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(R)-4-Methyloxazolidin-2-one → (R)-3-{3,5-difluoro-4-[4-(5-methylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-4-methyloxazolidin-2-one

HRID 1804387
Notes
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Reaction equation

HRID 1804387 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][N:18]=3)[CH2:13][CH2:12]2)=[O:10])=[C:4]([F:24])[CH:3]=1.[CH3:25][C@@H:26]1[CH2:30][O:29][C:28](=[O:31])[NH:27]1>>[F:24][C:4]1[CH:3]=[C:2]([N:27]2[C@H:26]([CH3:25])[CH2:30][O:29][C:28]2=[O:31])[CH:7]=[C:6]([F:8])[C:5]=1[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][N:18]=2)[CH2:13][CH2:12]1)=[O:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 2734858(R)-4-Methyloxazolidin-2-oneHCID 58484560(4-Bromo-2,6-difluorophenyl)[4-(5-methylpyridin-2-yl)piperazin-1-yl]methanone

Product 1

HCID 58484766(R)-3-{3,5-difluoro-4-[4-(5-methylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-4-methyloxazolidin-2-oneYield 67.1%

Procedure

By reaction and treatment in the same manner as in Example 110 and using (4-bromo-2,6-difluorophenyl)[4-(5-methylpyridin-2-yl)piperazin-1-yl]methanone (393 mg) described in Preparation Example 185 and (R)-4-methyloxazolidin-2-one (132 mg) described in Preparation Example 25, the title compound (277 mg) was obtained.

Workup

  • customBy reaction and treatment in the same manner as in Example 110
  • customdescribed in Preparation Example 25
  • Sources & evidence

    ORD record
    ord-75a5c5dea19b4cf9abaf027a2bd0e553
    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