(R)-4-Methyloxazolidin-2-one → (R)-3-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]-3-(1,1-dioxo-1,2-thiazinan-2-yl)phenyl}-4-methyloxazolidin-2-one

HRID 1804292Notes

Reaction equation

HRID 1804292 reaction equation
Cl[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[CH2:29][CH2:28][CH2:27][CH2:26][S:25]2(=[O:31])=[O:30])[CH:3]=1.[CH3:32][C@@H:33]1[CH2:37][O:36][C:35](=[O:38])[NH:34]1>>[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:34]4[C@H:33]([CH3:32])[CH2:37][O:36][C:35]4=[O:38])=[CH:3][C:4]=3[N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][S:25]3(=[O:31])=[O:30])=[O:9])[CH2:11][CH2:12]2)=[N:17][CH:18]=[C:19]([CH3:23])[CH:20]=1

Participants

3

Reactant 2

HCID 2734858(R)-4-Methyloxazolidin-2-oneHCID 58484702[4-Chloro-2-(1,1-dioxo-1,2-thiazinan-2-yl)phenyl][4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone

Product 1

HCID 58484767(R)-3-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]-3-(1,1-dioxo-1,2-thiazinan-2-yl)phenyl}-4-methyloxazolidin-2-oneYield 31.6%

Procedure

By reaction and treatment in the same manner as in Example 201 and using [4-chloro-2-(1,1-dioxo-1,2-thiazinan-2-yl)phenyl][4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (218 mg) described in Preparation Example 128 and (R)-4-methyloxazolidin-2-one (47.6 mg) described in Preparation Example 25, the title compound (78.5 mg) was obtained.

Workup

  1. customBy reaction and treatment in the same manner as in Example 201
  2. customdescribed in Preparation Example 25

Sources & evidence

ORD record
ord-9cdb76e64a32434db677b132704c48e7
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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