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

HRID 1804248Notes

Reaction equation

HRID 1804248 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([CH3:25])[C:7]([N:10]3[CH2:15][CH2:14][N:13]([C:16]([C:18]4[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=4)=[O:17])[CH2:12][CH2:11]3)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.[CH2:26]([C@@H:28]1[CH2:32][O:31][C:30](=[O:33])[NH:29]1)[CH3:27]>>[CH:1]1([C:4]2[CH:5]=[C:6]([CH3:25])[C:7]([N:10]3[CH2:15][CH2:14][N:13]([C:16]([C:18]4[CH:23]=[CH:22][C:21]([N:29]5[C@H:28]([CH2:26][CH3:27])[CH2:32][O:31][C:30]5=[O:33])=[CH:20][CH:19]=4)=[O:17])[CH2:12][CH2:11]3)=[N:8][CH:9]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 641503(4R)-4-ethyl-1,3-oxazolidin-2-oneHCID 58484841[4-(5-Cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl](4-iodophenyl)methanone

Product 1

HCID 67380709(R)-3-{4-[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-4-ethyloxazolidin-2-oneYield 67.2%

Procedure

By reaction and treatment in the same manner as in Example 149 and using [4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl](4-iodophenyl)methanone (447 mg) described in Preparation Example 97 and (R)-4-ethyloxazolidin-2-one (138 mg) described in Preparation Example 26, the title compound (292 mg) was obtained.

Workup

  1. customBy reaction and treatment in the same manner as in Example 149
  2. customdescribed in Preparation Example 26

Sources & evidence

ORD record
ord-085d66809f9d46b0bdc1c459560ea78e
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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