(4R)-4-Propyl-2-oxazolidinone → (R)-3-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]-3-(1,1-dioxoisothiazolidin-2-yl)phenyl}-4-propyloxazolidin-2-one

HRID 1804277Notes

Reaction equation

HRID 1804277 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[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][N:17]=3)[CH2:12][CH2:11]2)=[O:9])=[C:4]([N:24]2[CH2:28][CH2:27][CH2:26][S:25]2(=[O:30])=[O:29])[CH:3]=1.[CH2:31]([C@@H:34]1[CH2:38][O:37][C:36](=[O:39])[NH:35]1)[CH2:32][CH3:33]>>[CH3:22][C:21]1[C:16]([N:13]2[CH2:14][CH2:15][N:10]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([N:35]4[C@H:34]([CH2:31][CH2:32][CH3:33])[CH2:38][O:37][C:36]4=[O:39])=[CH:3][C:4]=3[N:24]3[CH2:28][CH2:27][CH2:26][S:25]3(=[O:30])=[O:29])=[O:9])[CH2:11][CH2:12]2)=[N:17][CH:18]=[C:19]([CH3:23])[CH:20]=1

Participants

3

Reactant 2

HCID 2734859(4R)-4-Propyl-2-oxazolidinoneHCID 58484716[4-Bromo-2-(1,1-dioxoisothiazolidin-2-yl)phenyl][4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone

Product 1

HCID 58484712(R)-3-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]-3-(1,1-dioxoisothiazolidin-2-yl)phenyl}-4-propyloxazolidin-2-oneYield 69.7%

Procedure

By reaction and treatment in the same manner as in Example 1 and using [4-bromo-2-(1,1-dioxoisothiazolidin-2-yl)phenyl][4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (247 mg) described in Preparation Example 118 and (R)-4-propyloxazolidin-2-one (64.58 mg) described in Preparation Example 29, the title compound (188.8 mg) was obtained.

Workup

  1. customBy reaction and treatment in the same manner as in Example 1
  2. customdescribed in Preparation Example 29

Sources & evidence

ORD record
ord-a95ec1d79b814d5d9257257cc917b918
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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