(4R)-4-ethyl-1,3-oxazolidin-2-one → (R)-3-{4-[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazine-1-carbonyl]-3-(1,1-dioxoisothiazolidin-2-yl)phenyl}-4-ethyloxazolidin-2-one

HRID 1804368Notes

Reaction equation

HRID 1804368 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]([CH:23]4[CH2:25][CH2:24]4)=[CH:18][N:17]=3)[CH2:12][CH2:11]2)=[O:9])=[C:4]([N:26]2[CH2:30][CH2:29][CH2:28][S:27]2(=[O:32])=[O:31])[CH:3]=1.[CH2:33]([C@@H:35]1[CH2:39][O:38][C:37](=[O:40])[NH:36]1)[CH3:34]>>[CH:23]1([C:19]2[CH:20]=[C:21]([CH3:22])[C:16]([N:13]3[CH2:14][CH2:15][N:10]([C:8]([C:5]4[CH:6]=[CH:7][C:2]([N:36]5[C@H:35]([CH2:33][CH3:34])[CH2:39][O:38][C:37]5=[O:40])=[CH:3][C:4]=4[N:26]4[CH2:30][CH2:29][CH2:28][S:27]4(=[O:32])=[O:31])=[O:9])[CH2:11][CH2:12]3)=[N:17][CH:18]=2)[CH2:25][CH2:24]1

Participants

3

Reactant 2

HCID 641503(4R)-4-ethyl-1,3-oxazolidin-2-oneHCID 58484554[4-Bromo-2-(1,1-dioxoisothiazolidin-2-yl)phenyl][4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl]methanone

Product 1

HCID 58484781(R)-3-{4-[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazine-1-carbonyl]-3-(1,1-dioxoisothiazolidin-2-yl)phenyl}-4-ethyloxazolidin-2-oneYield 85.7%

Procedure

By reaction and treatment in the same manner as in Example 149 and using [4-bromo-2-(1,1-dioxoisothiazolidin-2-yl)phenyl][4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl]methanone (519 mg) described in Preparation Example 179 and (R)-4-ethyloxazolidin-2-one (138 mg) described in Preparation Example 26, the title compound (474 mg) was obtained.

Workup

  1. customBy reaction and treatment in the same manner as in Example 149
  2. customdescribed in Preparation Example 26

Sources & evidence

ORD record
ord-72586e7dae754504afa8bec6000e6658
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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