(R)-2-methoxy-4-(4-methyl-2-oxooxazolidin-3-yl)benzoic acid → (R)-3-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]-3-methoxyphenyl}-4-methyloxazolidin-2-one hydrochloride

HRID 1804224Notes

Reaction equation

HRID 1804224 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([N:12]2[C@H:16]([CH3:17])[CH2:15][O:14][C:13]2=[O:18])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.[ClH:19].[CH3:20][C:21]1[C:22]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[N:23][CH:24]=[C:25]([CH3:27])[CH:26]=1>>[ClH:19].[CH3:20][C:21]1[C:22]([N:28]2[CH2:29][CH2:30][N:31]([C:5]([C:4]3[CH:8]=[CH:9][C:10]([N:12]4[C@H:16]([CH3:17])[CH2:15][O:14][C:13]4=[O:18])=[CH:11][C:3]=3[O:2][CH3:1])=[O:7])[CH2:32][CH2:33]2)=[N:23][CH:24]=[C:25]([CH3:27])[CH:26]=1

Participants

3

Reactant 2

HCID 58484787(R)-2-methoxy-4-(4-methyl-2-oxooxazolidin-3-yl)benzoic acidHCID 673813791-(3,5-Dimethylpyridin-2-yl)piperazine hydrochloride

Product 1

HCID 67381134(R)-3-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]-3-methoxyphenyl}-4-methyloxazolidin-2-one hydrochlorideYield 37.8%

Procedure

By reaction and treatment in the same manner as in Example 87 and using (R)-2-methoxy-4-(4-methyl-2-oxooxazolidin-3-yl)benzoic acid (1.1 g) described in Preparation Example 45 and 1-(3,5-dimethylpyridin-2-yl)piperazine hydrochloride (956 mg) described in Preparation Example 64, the title compound (731 mg) was obtained.

Workup

  1. customBy reaction and treatment in the same manner as in Example 87
  2. customdescribed in Preparation Example 64

Sources & evidence

ORD record
ord-5121c145ef64449aa36863d5d889b4ac
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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