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

HRID 1804213Notes

Reaction equation

HRID 1804213 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:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)=[N:23][CH:24]=[C:25]([CH:27]3[CH2:29][CH2:28]3)[CH:26]=2)[CH2:20][CH2:19]1>>[ClH:17].[CH:18]1([C:21]2[C:22]([N:30]3[CH2:31][CH2:32][N:33]([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])[CH2:34][CH2:35]3)=[N:23][CH:24]=[C:25]([CH:27]3[CH2:29][CH2:28]3)[CH:26]=2)[CH2:19][CH2:20]1

Participants

3

Reactant 2

HCID 58484719(R)-4-(4-methyl-2-oxooxazolidin-3-yl)benzoic acidHCID 673810941-(3,5-Dicyclopropylpyridin-2-yl)piperazine hydrochloride

Product 1

HCID 67447499(R)-3-{4-[4-(3,5-dicyclopropylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-4-methyloxazolidin-2-one hydrochlorideYield 152.5%

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-(3,5-dicyclopropylpyridin-2-yl)piperazine hydrochloride (487 mg) described in Preparation Example 50, the title compound (736 mg) was obtained.

Workup

  1. customBy reaction and treatment in the same manner as in Example 87
  2. customdescribed in Preparation Example 50

Sources & evidence

ORD record
ord-89f6f00a346c45eeb76f643cb309eaac
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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