(4R)-4-ethyl-1,3-oxazolidin-2-one → (R)-3-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]-3-fluorophenyl}-4-ethyloxazolidin-2-one

HRID 1804199Notes

Reaction equation

HRID 1804199 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][N:17]=3)[CH2:12][CH2:11]2)=[O:9])=[C:4]([F:24])[CH:3]=1.[CH2:25]([C@@H:27]1[CH2:31][O:30][C:29](=[O:32])[NH:28]1)[CH3:26]>>[CH3:22][C:21]1[C:16]([N:13]2[CH2:14][CH2:15][N:10]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([N:28]4[C@H:27]([CH2:25][CH3:26])[CH2:31][O:30][C:29]4=[O:32])=[CH:3][C:4]=3[F:24])=[O:9])[CH2:11][CH2:12]2)=[N:17][CH:18]=[C:19]([CH3:23])[CH:20]=1

Participants

3

Reactant 2

HCID 641503(4R)-4-ethyl-1,3-oxazolidin-2-oneHCID 58484626(4-Bromo-2-fluorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone

Product 1

HCID 67380800(R)-3-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]-3-fluorophenyl}-4-ethyloxazolidin-2-oneYield 19.3%

Procedure

By reaction and treatment in the same manner as in Example 1 and using (4-bromo-2-fluorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (1.6 g) described in Preparation Example 65 and (R)-4-ethyloxazolidin-2-one (553 mg) described in Preparation Example 26, the title compound (336 mg) was obtained.

Workup

  1. customBy reaction and treatment in the same manner as in Example 1
  2. customdescribed in Preparation Example 26

Sources & evidence

ORD record
ord-7696d9101ded4962a39dd6a0a92cf564
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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