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3-Methyl-5-isopropylhydantoin → 1-{5-[4-(3,5-Dimethylpyridin-2-yl)piperazine-1-carbonyl]pyridin-2-yl}-5-isopropyl-3-methylimidazolidine-2,4-dione

HRID 2411921
Notes
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Reaction equation

HRID 2411921 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:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][N:17]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[CH:24]([CH:27]1[NH:31][C:30](=[O:32])[N:29]([CH3:33])[C:28]1=[O:34])([CH3:26])[CH3:25]>>[CH3:22][C:21]1[C:16]([N:13]2[CH2:14][CH2:15][N:10]([C:8]([C:5]3[CH:4]=[CH:3][C:2]([N:31]4[CH:27]([CH:24]([CH3:25])[CH3:26])[C:28](=[O:34])[N:29]([CH3:33])[C:30]4=[O:32])=[N:7][CH:6]=3)=[O:9])[CH2:11][CH2:12]2)=[N:17][CH:18]=[C:19]([CH3:23])[CH:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 534258423-Methyl-5-isopropylhydantoinHCID 58484661(6-Bromopyridin-3-yl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone

Product 1

HCID 712528061-{5-[4-(3,5-Dimethylpyridin-2-yl)piperazine-1-carbonyl]pyridin-2-yl}-5-isopropyl-3-methylimidazolidine-2,4-dioneYield 55%

Procedure

Using (6-bromopyridin-3-yl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (150 mg) described in Preparation Example 127 and 5-isopropyl-3-methylimidazolidine-2,4-dione (69 mg) described in Preparation Example 216 and by the reaction and treatment in the same manner as in Example 536, the title compound (99 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 216 and by the reaction and treatment in the same manner as in Example 536

Sources & evidence

ORD record
ord-58b9c647c702496db18c853f6d644b65
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08816079B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes