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

HRID 2411920Notes

Reaction equation

HRID 2411920 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.[CH:25]([CH:28]1[NH:32][C:31](=[O:33])[N:30]([CH3:34])[C:29]1=[O:35])([CH3:27])[CH3:26]>>[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:32]4[CH:28]([CH:25]([CH3:26])[CH3:27])[C:29](=[O:35])[N:30]([CH3:34])[C:31]4=[O:33])=[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 534258423-Methyl-5-isopropylhydantoinHCID 58484626(4-Bromo-2-fluorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone

Product 1

HCID 712526721-{4-[4-(3,5-Dimethylpyridin-2-yl)piperazine-1-carbonyl]-3-fluorophenyl}-5-isopropyl-3-methylimidazolidine-2,4-dioneYield 59.3%

Procedure

Using (4-bromo-2-fluorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (157 mg) described in Preparation Example 114 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 (111 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-43b6d811535d4b33b50155d4a9466c57
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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