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

HRID 1804303Notes

Reaction equation

HRID 1804303 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[C:23]([CH3:24])=[CH:22][C:19]([C:20]#[N:21])=[CH:18][N:17]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[CH3:25][C@@H:26]1[CH2:30][O:29][C:28](=[O:31])[NH:27]1>>[C:20]([C:19]1[CH:22]=[C:23]([CH3:24])[C:16]([N:13]2[CH2:14][CH2:15][N:10]([C:8]([C:5]3[CH:4]=[CH:3][C:2]([N:27]4[C@H:26]([CH3:25])[CH2:30][O:29][C:28]4=[O:31])=[N:7][CH:6]=3)=[O:9])[CH2:11][CH2:12]2)=[N:17][CH:18]=1)#[N:21]

Participants

3

Reactant 2

HCID 2734858(R)-4-Methyloxazolidin-2-oneHCID 584845186-[4-(6-Bromopyridine-3-carbonyl)piperazin-1-yl]-5-methylnicotinonitrile

Product 1

HCID 46190279(R)-3-{5-[4-(5-cyano-3-methylpyridin-2-yl)piperazine-1-carbonyl]pyridin-2-yl}-4-methyloxazolidin-2-oneYield 80.8%

Procedure

By reaction and treatment in the same manner as in Example 1 and using 6-[4-(6-bromopyridine-3-carbonyl)piperazin-1-yl]-5-methylnicotinonitrile (200 mg) described in Preparation Example 131 and (R)-4-methyloxazolidin-2-one (79 mg) described in Preparation Example 25, the title compound (170 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-f12ef8664a8346c18b084e125c29b52e
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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