5,5-Dimethyloxazolin-2-one → 3-{3-(1,1-Dioxoisothiazolidin-2-yl)-4-[4-(5-ethyl-3-methylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-5,5-dimethyloxazolidin-2-one

HRID 1804375Notes

Reaction equation

HRID 1804375 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]([CH2:23][CH3:24])=[CH:18][N:17]=3)[CH2:12][CH2:11]2)=[O:9])=[C:4]([N:25]2[CH2:29][CH2:28][CH2:27][S:26]2(=[O:31])=[O:30])[CH:3]=1.[CH3:32][C:33]1([CH3:39])[O:37][C:36](=[O:38])[N:35]=[CH:34]1>>[O:30]=[S:26]1(=[O:31])[CH2:27][CH2:28][CH2:29][N:25]1[C:4]1[CH:3]=[C:2]([N:35]2[CH2:34][C:33]([CH3:39])([CH3:32])[O:37][C:36]2=[O:38])[CH:7]=[CH:6][C:5]=1[C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH2:23][CH3:24])=[CH:18][N:17]=2)[CH2:12][CH2:11]1)=[O:9]

Participants

3

Reactant 2

HCID 214647825,5-Dimethyloxazolin-2-oneHCID 58484567[4-Bromo-2-(1,1-dioxoisothiazolidin-2-yl)phenyl][4-(5-ethyl-3-methylpyridin-2-yl)piperazin-1-yl]methanone

Product 1

HCID 584847203-{3-(1,1-Dioxoisothiazolidin-2-yl)-4-[4-(5-ethyl-3-methylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-5,5-dimethyloxazolidin-2-oneYield 48.3%

Procedure

By reaction and treatment in the same manner as in Example 110 and using [4-bromo-2-(1,1-dioxoisothiazolidin-2-yl)phenyl][4-(5-ethyl-3-methylpyridin-2-yl)piperazin-1-yl]methanone (761 mg) described in Preparation Example 180 and 5,5-dimethyloxazolin-2-one (207 mg) described in Preparation Example 43, the title compound (392 mg) was obtained.

Workup

  1. customBy reaction and treatment in the same manner as in Example 110
  2. customdescribed in Preparation Example 43

Sources & evidence

ORD record
ord-d67b0aef1454447884ab84ce99c96438
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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