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

HRID 1804210Notes

Reaction equation

HRID 1804210 reaction equation
[CH3:1][C@@H:2]1[CH2:6][O:5][C:4](=[O:7])[N:3]1[C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1.[ClH:17].[CH:18]1([C:21]2[C:22]([N:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)=[N:23][CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=2)[CH2:20][CH2:19]1>>[ClH:17].[CH:18]1([C:21]2[C:22]([N:31]3[CH2:36][CH2:35][N:34]([C:12]([C:11]4[CH:10]=[CH:9][C:8]([N:3]5[C@H:2]([CH3:1])[CH2:6][O:5][C:4]5=[O:7])=[CH:16][CH:15]=4)=[O:14])[CH2:33][CH2:32]3)=[N:23][CH:24]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:26]=2)[CH2:19][CH2:20]1

Participants

3

Reactant 2

HCID 58484719(R)-4-(4-methyl-2-oxooxazolidin-3-yl)benzoic acidHCID 673807791-(3-Cyclopropyl-5-trifluoromethylpyridin-2-yl)piperazine hydrochloride

Product 1

HCID 67380940(R)-3-{4-[4-(3-cyclopropyl-5-trifluoromethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-4-methyloxazolidin-2-one hydrochlorideYield 111.9%

Procedure

By reaction and treatment in the same manner as in Example 87 and using (R)-4-(4-methyl-2-oxooxazolidin-3-yl)benzoic acid (221 mg) described in Preparation Example 37 and 1-(3-cyclopropyl-5-trifluoromethylpyridin-2-yl)piperazine hydrochloride (615 mg) described in Preparation Example 76, the title compound (571 mg) was obtained.

Workup

  1. customBy reaction and treatment in the same manner as in Example 87
  2. customdescribed in Preparation Example 76

Sources & evidence

ORD record
ord-086d19a35caf4e8eb6b96d3be9a694d9
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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