(S)-5-methyloxazolidin-2-one → (S)-3-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]-3,5-difluorophenyl}-5-methyloxazolidin-2-one

HRID 1804254Notes

Reaction equation

HRID 1804254 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[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][N:18]=3)[CH2:13][CH2:12]2)=[O:10])=[C:4]([F:25])[CH:3]=1.[CH3:26][C@@H:27]1[O:31][C:30](=[O:32])[NH:29][CH2:28]1>>[CH3:23][C:22]1[C:17]([N:14]2[CH2:15][CH2:16][N:11]([C:9]([C:5]3[C:6]([F:8])=[CH:7][C:2]([N:29]4[CH2:28][C@H:27]([CH3:26])[O:31][C:30]4=[O:32])=[CH:3][C:4]=3[F:25])=[O:10])[CH2:12][CH2:13]2)=[N:18][CH:19]=[C:20]([CH3:24])[CH:21]=1

Participants

3

Reactant 2

HCID 21794663(S)-5-methyloxazolidin-2-oneHCID 58484761(4-Bromo-2,6-difluorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone

Product 1

HCID 58484592(S)-3-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]-3,5-difluorophenyl}-5-methyloxazolidin-2-oneYield 52.2%

Procedure

By reaction and treatment in the same manner as in Example 1 and using (4-bromo-2,6-difluorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (615 mg) described in Preparation Example 60 and (S)-5-methyloxazolidin-2-one (243 mg) described in Preparation Example 42, the title compound (337 mg) was obtained.

Workup

  1. customBy reaction and treatment in the same manner as in Example 1
  2. customdescribed in Preparation Example 42

Sources & evidence

ORD record
ord-7d1b6795601e45c99923763d30ef9e0e
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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