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5,5-Dimethyloxazolin-2-one → 3-{4-[4-(5-Cyclopropylpyridin-2-yl)piperazine-1-carbonyl]-3-fluorophenyl}-5,5-dimethyloxazolidin-2-one

HRID 1804391
Notes
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Reaction equation

HRID 1804391 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([CH:22]4[CH2:24][CH2:23]4)=[CH:18][N:17]=3)[CH2:12][CH2:11]2)=[O:9])=[C:4]([F:25])[CH:3]=1.[CH3:26][C:27]1([CH3:33])[O:31][C:30](=[O:32])[N:29]=[CH:28]1>>[CH:22]1([C:19]2[CH:20]=[CH:21][C:16]([N:13]3[CH2:14][CH2:15][N:10]([C:8]([C:5]4[CH:6]=[CH:7][C:2]([N:29]5[CH2:28][C:27]([CH3:33])([CH3:26])[O:31][C:30]5=[O:32])=[CH:3][C:4]=4[F:25])=[O:9])[CH2:11][CH2:12]3)=[N:17][CH:18]=2)[CH2:24][CH2:23]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 214647825,5-Dimethyloxazolin-2-oneHCID 58484657(4-Bromo-2-fluorophenyl)[4-(5-cyclopropylpyridin-2-yl)piperazin-1-yl]methanone

Product 1

HCID 584846503-{4-[4-(5-Cyclopropylpyridin-2-yl)piperazine-1-carbonyl]-3-fluorophenyl}-5,5-dimethyloxazolidin-2-oneYield 43.2%

Procedure

By reaction and treatment in the same manner as in Example 110 and using (4-bromo-2-fluorophenyl)[4-(5-cyclopropylpyridin-2-yl)piperazin-1-yl]methanone (606 mg) described in Preparation Example 188 and 5,5-dimethyloxazolin-2-one (207 mg) described in Preparation Example 43, the title compound (284 mg) was obtained.

Workup

  • customBy reaction and treatment in the same manner as in Example 110
  • customdescribed in Preparation Example 43
  • Sources & evidence

    ORD record
    ord-9035ee756bfb496680220b9927b26c74
    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