3,5,5-Trimethylimidazolidine-2,4-dione → 1-{4-[4-(3,5-Dimethylpyridin-2-yl)piperazine-1-carbonyl]-3-fluorophenyl}-3,5,5-trimethylimidazolidine-2,4-dione

HRID 2411925Notes

Reaction equation

HRID 2411925 reaction equation
Br[C:2]1[CH: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])=[C:4]([F:24])[CH:3]=1.[CH3:25][N:26]1[C:30](=[O:31])[C:29]([CH3:33])([CH3:32])[NH:28][C:27]1=[O:34]>>[CH3:22][C:21]1[C:16]([N:13]2[CH2:14][CH2:15][N:10]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([N:28]4[C:29]([CH3:33])([CH3:32])[C:30](=[O:31])[N:26]([CH3:25])[C:27]4=[O:34])=[CH:3][C:4]=3[F:24])=[O:9])[CH2:11][CH2:12]2)=[N:17][CH:18]=[C:19]([CH3:23])[CH:20]=1

Participants

3

Reactant 2

HCID 2375603,5,5-Trimethylimidazolidine-2,4-dioneHCID 58484626(4-Bromo-2-fluorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone

Product 1

HCID 712523021-{4-[4-(3,5-Dimethylpyridin-2-yl)piperazine-1-carbonyl]-3-fluorophenyl}-3,5,5-trimethylimidazolidine-2,4-dioneYield 16.5%

Procedure

Using (4-bromo-2-fluorophenyl) [4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (157 mg) described in Preparation Example 114 and 3,5,5-trimethylimidazolidine-2,4-dione (63 mg) described in Preparation Example 218 and by the reaction and treatment in the same manner as in Example 536, the title compound (30 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 218 and by the reaction and treatment in the same manner as in Example 536

Sources & evidence

ORD record
ord-e16a136af3fc4dfa9fb755515046468f
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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