(R)-4-Methyloxazolidin-2-one → (R)-3-{4-[4-(5-cyclopropylpyridin-2-yl)piperazine-1-carbonyl]-3,5-difluorophenyl}-4-methyloxazolidin-2-one

HRID 1804393Notes

Reaction equation

HRID 1804393 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]4[CH2:25][CH2:24]4)=[CH:19][N:18]=3)[CH2:13][CH2:12]2)=[O:10])=[C:4]([F:26])[CH:3]=1.[CH3:27][C@@H:28]1[CH2:32][O:31][C:30](=[O:33])[NH:29]1>>[CH:23]1([C:20]2[CH:21]=[CH:22][C:17]([N:14]3[CH2:15][CH2:16][N:11]([C:9]([C:5]4[C:6]([F:8])=[CH:7][C:2]([N:29]5[C@H:28]([CH3:27])[CH2:32][O:31][C:30]5=[O:33])=[CH:3][C:4]=4[F:26])=[O:10])[CH2:12][CH2:13]3)=[N:18][CH:19]=2)[CH2:25][CH2:24]1

Participants

3

Reactant 2

HCID 2734858(R)-4-Methyloxazolidin-2-oneHCID 58484548(4-Bromo-2,6-difluorophenyl)[4-(5-cyclopropylpyridin-2-yl)piperazin-1-yl]methanone

Product 1

HCID 58484551(R)-3-{4-[4-(5-cyclopropylpyridin-2-yl)piperazine-1-carbonyl]-3,5-difluorophenyl}-4-methyloxazolidin-2-oneYield 58.1%

Procedure

By reaction and treatment in the same manner as in Example 110 and using (4-bromo-2,6-difluorophenyl)[4-(5-cyclopropylpyridin-2-yl)piperazin-1-yl]methanone (422 mg) described in Preparation Example 189 and (R)-4-methyloxazolidin-2-one (134 mg) described in Preparation Example 25, the title compound (257 mg) was obtained.

Workup

  1. customBy reaction and treatment in the same manner as in Example 110
  2. customdescribed in Preparation Example 25

Sources & evidence

ORD record
ord-e7875cb73b3f4390acf124101819ec23
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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