(R)-4-Methyloxazolidin-2-one → (R)-3-{4-[4-(5-cyano-3-methylpyridin-2-yl)piperazine-1-carbonyl]-3-methylphenyl}-4-methyloxazolidin-2-one

HRID 1804307Notes

Reaction equation

HRID 1804307 reaction equation
Br[C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[C:21]([CH3:22])=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=3)[CH2:10][CH2:9]2)=[O:7])=[C:4]([CH3:25])[CH:3]=1.[CH3:26][C@@H:27]1[CH2:31][O:30][C:29](=[O:32])[NH:28]1>>[C:18]([C:17]1[CH:20]=[C:21]([CH3:22])[C:14]([N:11]2[CH2:12][CH2:13][N:8]([C:6]([C:5]3[CH:23]=[CH:24][C:2]([N:28]4[C@H:27]([CH3:26])[CH2:31][O:30][C:29]4=[O:32])=[CH:3][C:4]=3[CH3:25])=[O:7])[CH2:9][CH2:10]2)=[N:15][CH:16]=1)#[N:19]

Participants

3

Reactant 2

HCID 2734858(R)-4-Methyloxazolidin-2-oneHCID 584846766-[4-(4-Bromo-2-methylbenzoyl)piperazin-1-yl]-5-methylnicotinonitrile

Product 1

HCID 58484809(R)-3-{4-[4-(5-cyano-3-methylpyridin-2-yl)piperazine-1-carbonyl]-3-methylphenyl}-4-methyloxazolidin-2-oneYield 65.7%

Procedure

By reaction and treatment in the same manner as in Example 1 and using 6-[4-(4-bromo-2-methylbenzoyl)piperazin-1-yl]-5-methylnicotinonitrile (210 mg) described in Preparation Example 133 and (R)-4-methyloxazolidin-2-one (80 mg) described in Preparation Example 25, the title compound (145 mg) was obtained.

Workup

  1. customBy reaction and treatment in the same manner as in Example 1
  2. customdescribed in Preparation Example 25

Sources & evidence

ORD record
ord-53f0ec013153455b804df5050dd25ef5
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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