(6-Bromopyridin-3-yl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone → 1-{5-[4-(3,5-Dimethylpyridin-2-yl)piperazine-1-carbonyl]pyridin-2-yl}-4,4-dimethylimidazolidin-2-one

HRID 2411862Notes

Reaction equation

HRID 2411862 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.C([N:32]1[C:36]([CH3:38])([CH3:37])[CH2:35][NH:34][C:33]1=[O:39])(=O)C1C=CC=CC=1>>[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:34]4[CH2:35][C:36]([CH3:38])([CH3:37])[NH:32][C:33]4=[O:39])=[N:7][CH:6]=3)=[O:9])[CH2:11][CH2:12]2)=[N:17][CH:18]=[C:19]([CH3:23])[CH:20]=1

Participants

3

Reactant 2

HCID 58484661(6-Bromopyridin-3-yl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanoneHCID 712521131-Benzoyl-5,5-dimethylimidazolidin-2-one

Product 1

HCID 712520741-{5-[4-(3,5-Dimethylpyridin-2-yl)piperazine-1-carbonyl]pyridin-2-yl}-4,4-dimethylimidazolidin-2-oneYield 36.7%

Procedure

Using (6-bromopyridin-3-yl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (150 mg) described in Preparation Example 127 and 1-benzoyl-5,5-dimethylimidazolidin-2-one (105 mg) described in Preparation Example 58 and by the reaction and treatment in the same manner as in Example 509 to give the title compound (60 mg) produced by debenzoylation that simultaneously proceeded during the reaction.

Workup

  1. customdescribed in Preparation Example 58 and by the reaction and treatment in the same manner as in Example 509

Sources & evidence

ORD record
ord-9347aad7969f48e7a8b2d86ef9ee849e
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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