(4R)-4-ethyl-1,3-oxazolidin-2-one → (R)-3-{5-[4-(4-chlorobenzoyl)piperidine-1-carbonyl]pyridin-2-yl}-4-ethyloxazolidin-2-one

HRID 1803970Notes

Reaction equation

HRID 1803970 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][CH:13]([C:16](=[O:24])[C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[CH2:25]([C@@H:27]1[CH2:31][O:30][C:29](=[O:32])[NH:28]1)[CH3:26]>>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([C:16]([CH:13]2[CH2:14][CH2:15][N:10]([C:8]([C:5]3[CH:4]=[CH:3][C:2]([N:28]4[C@H:27]([CH2:25][CH3:26])[CH2:31][O:30][C:29]4=[O:32])=[N:7][CH:6]=3)=[O:9])[CH2:11][CH2:12]2)=[O:24])=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 641503(4R)-4-ethyl-1,3-oxazolidin-2-oneHCID 58484839(6-Bromopyridin-3-yl)[4-(4-chlorobenzoyl)piperidin-1-yl]methanone

Product 1

HCID 54755118(R)-3-{5-[4-(4-chlorobenzoyl)piperidine-1-carbonyl]pyridin-2-yl}-4-ethyloxazolidin-2-oneYield 61.7%

Procedure

By reaction and treatment in the same manner as in Preparation Example 31 and using (6-bromopyridin-3-yl)[4-(4-chlorobenzoyl)piperidin-1-yl]methanone (2 g) described in Preparation Example 23 and (R)-4-ethyloxazolidin-2-one (300 mg) described in Preparation Example 26, the title compound (710 mg) was obtained.

Workup

  1. customBy reaction and treatment in the same manner
  2. customas in Preparation Example 31
  3. customdescribed in Preparation Example 26

Sources & evidence

ORD record
ord-efb87ac04d4b4ee1b8144dbfbafc1b6e
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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