(R)-4-(4-isopropyl-2-oxooxazolidin-3-yl)benzoic acid → (R)-4-isopropyl-3-{4-[4-(3-methyl-5-trifluoromethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}oxazolidin-2-one

HRID 1804190Notes

Reaction equation

HRID 1804190 reaction equation
[CH:1]([C@@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=1)([CH3:3])[CH3:2].[CH3:19][C:20]1[C:21]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[N:22][CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1>>[CH:1]([C@@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:10]1[CH:11]=[CH:12][C:13]([C:14]([N:33]2[CH2:34][CH2:35][N:30]([C:21]3[C:20]([CH3:19])=[CH:25][C:24]([C:26]([F:29])([F:27])[F:28])=[CH:23][N:22]=3)[CH2:31][CH2:32]2)=[O:16])=[CH:17][CH:18]=1)([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 58484694(R)-4-(4-isopropyl-2-oxooxazolidin-3-yl)benzoic acidHCID 584847291-(3-Methyl-5-trifluoromethylpyridin-2-yl)piperazine

Product 1

HCID 67380990(R)-4-isopropyl-3-{4-[4-(3-methyl-5-trifluoromethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}oxazolidin-2-oneYield 30.7%

Procedure

By reaction and treatment in the same manner as in Example 29 and using (R)-4-(4-isopropyl-2-oxooxazolidin-3-yl)benzoic acid (499 mg) described in Preparation Example 18 and 1-(3-methyl-5-trifluoromethylpyridin-2-yl)piperazine (490 mg) described in Preparation Example 51, the title compound (292 mg) was obtained.

Workup

  1. customBy reaction and treatment in the same manner as in Example 29
  2. customdescribed in Preparation Example 51

Sources & evidence

ORD record
ord-777b159fbf0b40bb9066bac907350dc0
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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