(R)-4-Methyloxazolidin-2-one → (R)-3-{5-chloro-4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]-2-fluorophenyl}-4-methyloxazolidin-2-one hydrochloride

HRID 1804216Notes

Reaction equation

HRID 1804216 reaction equation
Br[C:2]1[C:7]([F:8])=[CH:6][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]([Cl:25])[CH:3]=1.[CH3:26][C@@H:27]1[CH2:31][O:30][C:29](=[O:32])[NH:28]1>>[ClH:25].[Cl:25][C:4]1[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])=[CH:6][C:7]([F:8])=[C:2]([N:28]2[C@H:27]([CH3:26])[CH2:31][O:30][C:29]2=[O:32])[CH:3]=1

Participants

3

Reactant 2

HCID 2734858(R)-4-Methyloxazolidin-2-oneHCID 58484674(4-Bromo-2-chloro-5-fluorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone

Product 1

HCID 67380907(R)-3-{5-chloro-4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]-2-fluorophenyl}-4-methyloxazolidin-2-one hydrochlorideYield 40.8%

Procedure

By reaction and treatment in the same manner as in Example 79 and using (4-bromo-2-chloro-5-fluorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (1.5 g) described in Preparation Example 72 and (R)-4-methyloxazolidin-2-one (400 mg) described in Preparation Example 25, the title compound (347 mg) was obtained.

Workup

  1. customBy reaction and treatment in the same manner as in Example 79
  2. customdescribed in Preparation Example 25

Sources & evidence

ORD record
ord-184515ae8d88460dbee31d903ab7e830
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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