(S)-5-methyloxazolidin-2-one → (S)-3-{4-[4-(3,5-dicyclopropylpyridin-2-yl)piperazine-1-carbonyl]-3-methanesulfonylphenyl}-5-methyloxazolidin-2-one

HRID 1804241Notes

Reaction equation

HRID 1804241 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]([CH:22]4[CH2:24][CH2:23]4)=[CH:20][C:19]([CH:25]4[CH2:27][CH2:26]4)=[CH:18][N:17]=3)[CH2:12][CH2:11]2)=[O:9])=[C:4]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:3]=1.[CH3:32][C@@H:33]1[O:37][C:36](=[O:38])[NH:35][CH2:34]1>>[CH:22]1([C:21]2[C:16]([N:13]3[CH2:14][CH2:15][N:10]([C:8]([C:5]4[CH:6]=[CH:7][C:2]([N:35]5[CH2:34][C@H:33]([CH3:32])[O:37][C:36]5=[O:38])=[CH:3][C:4]=4[S:28]([CH3:31])(=[O:30])=[O:29])=[O:9])[CH2:11][CH2:12]3)=[N:17][CH:18]=[C:19]([CH:25]3[CH2:27][CH2:26]3)[CH:20]=2)[CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 21794663(S)-5-methyloxazolidin-2-oneHCID 58484601(4-Bromo-2-methanesulfonylphenyl)[4-(3,5-dicyclopropylpyridin-2-yl)piperazin-1-yl]methanone

Product 1

HCID 67380870(S)-3-{4-[4-(3,5-dicyclopropylpyridin-2-yl)piperazine-1-carbonyl]-3-methanesulfonylphenyl}-5-methyloxazolidin-2-oneYield 62.1%

Procedure

By reaction and treatment in the same manner as in Example 111 and using (4-bromo-2-methanesulfonylphenyl)[4-(3,5-dicyclopropylpyridin-2-yl)piperazin-1-yl]methanone (400 mg) described in Preparation Example 89 and (S)-5-methyloxazolidin-2-one (80.2 mg) described in Preparation Example 42, the title compound (258.4 mg) was obtained.

Workup

  1. customBy reaction and treatment in the same manner as in Example 111
  2. customdescribed in Preparation Example 42

Sources & evidence

ORD record
ord-59a7f748137549019f59a4c140776456
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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