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

HRID 1804211Notes

Reaction equation

HRID 1804211 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N:12]1[C@H:16]([CH3:17])[CH2:15][O:14][C:13]1=[O:18])[C:6]([OH:8])=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:6]([C:5]3[CH:9]=[CH:10][C:11]([N:12]4[C@H:16]([CH3:17])[CH2:15][O:14][C:13]4=[O:18])=[C:3]([O:2][CH3:1])[CH:4]=3)=[O:8])[CH2:32][CH2:33]2)=[N:23][CH:24]=[C:25]([CH3:27])[CH:26]=1

Participants

3

Reactant 2

HCID 58484801(R)-3-methoxy-4-(4-methyl-2-oxooxazolidin-3-yl)benzoic acidHCID 673813791-(3,5-Dimethylpyridin-2-yl)piperazine hydrochloride

Product 1

HCID 67380763(R)-3-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]-2-methoxyphenyl}-4-methyloxazolidin-2-one hydrochlorideYield 45.7%

Procedure

By reaction and treatment in the same manner as in Example 87 and using (R)-3-methoxy-4-(4-methyl-2-oxooxazolidin-3-yl)benzoic acid (1 g) described in Preparation Example 46 and 1-(3,5-dimethylpyridin-2-yl)piperazine hydrochloride (956 mg) described in Preparation Example 64, the title compound (838 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-90a759e1eb1545449132415eaac2e119
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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