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

HRID 1804217Notes

Reaction equation

HRID 1804217 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.Cl.[CH3:18][C:19]1[C:20]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[N:21][CH:22]=[C:23]([CH3:25])[N:24]=1>>[CH3:18][C:19]1[C:20]([N:26]2[CH2:27][CH2:28][N:29]([C:12]([C:11]3[CH:10]=[CH:9][C:8]([N:3]4[C@H:2]([CH3:1])[CH2:6][O:5][C:4]4=[O:7])=[CH:16][CH:15]=3)=[O:14])[CH2:30][CH2:31]2)=[N:21][CH:22]=[C:23]([CH3:25])[N:24]=1

Participants

3

Reactant 2

HCID 58484719(R)-4-(4-methyl-2-oxooxazolidin-3-yl)benzoic acidHCID 67381341(3,5-Dimethylpyrazin-2-yl)piperazine hydrochloride

Product 1

HCID 67380726(R)-3-{4-[4-(3,5-dimethylpyrazin-2-yl)piperazine-1-carbonyl]phenyl]-4-methyloxazolidin-2-oneYield 64.2%

Procedure

By reaction and treatment in the same manner as in Example 49 and using (R)-4-(4-methyl-2-oxooxazolidin-3-yl)benzoic acid (422 mg) described in Preparation Example 37 and 1-(3,5-dimethylpyrazin-2-yl)piperazine hydrochloride (457 mg) described in Preparation Example 59, the title compound (484 mg) was obtained.

Workup

  1. customBy reaction and treatment in the same manner as in Example 49
  2. customdescribed in Preparation Example 59

Sources & evidence

ORD record
ord-6fdce8319516459d898d2dcfd82245a5
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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