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Water → 3-[4-(2-Hydroxy-1,1-dimethylethyl)phenyl]-5,5-dimethyl-1-{[2-(pyridin-3-ylamino)-pyridin-4-yl]methyl}imidazolidine-2,4-dione

HRID 546630
Notes
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Reaction equation

HRID 546630 reaction equation
B#B.CSC.[CH3:6][C:7]1([CH3:40])[C:11](=[O:12])[N:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH3:24])([CH3:23])[C:20](O)=[O:21])=[CH:15][CH:14]=2)[C:9](=[O:25])[N:8]1[CH2:26][C:27]1[CH:32]=[CH:31][N:30]=[C:29]([NH:33][C:34]2[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=2)[CH:28]=1.O.[OH-].[Na+]>O1CCCC1.CO.Cl.C(OCC)(=O)C>[OH:21][CH2:20][C:19]([C:16]1[CH:17]=[CH:18][C:13]([N:10]2[C:11](=[O:12])[C:7]([CH3:40])([CH3:6])[N:8]([CH2:26][C:27]3[CH:32]=[CH:31][N:30]=[C:29]([NH:33][C:34]4[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=4)[CH:28]=3)[C:9]2=[O:25])=[CH:14][CH:15]=1)([CH3:24])[CH3:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 22038413Diborane dimethylsulfideHCID 576259742-(4-{4,4-Dimethyl-2,5-dioxo-3-[2-(pyridin-3-ylamino)pyridin-4-ylmethyl]imidazolidin-1-yl}-phenyl)-2-methylpropionic acid

Product 1

HCID 576260103-[4-(2-Hydroxy-1,1-dimethylethyl)phenyl]-5,5-dimethyl-1-{[2-(pyridin-3-ylamino)-pyridin-4-yl]methyl}imidazolidine-2,4-dione
Yield 45%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.29 mL of diborane-dimethyl sulphide (2M in tetrahydrofuran) in 5 mL of tetrahydrofuran, under argon, at room temperature, is added 0.11 g of 2-(4-{4,4-dimethyl-2,5-dioxo-3-[2-(pyridin-3-ylamino)pyridin-4-ylmethyl]imidazolidin-1-yl}-phenyl)-2-methylpropionic acid obtained in stage f) below. The reaction medium is stirred at this same temperature for one hour and concentrated under reduced pressure. The residue obtained is taken up in 10 mL of methanol and 2 mL of 1N hydrochloric acid. The solution is concentrated under reduced pressure. The residue obtained is purified by Preparative LC/MS (gradient: acetonitrile/water/TFA 0.07%). The product obtained is taken up in 10 mL of ethyl acetate, 2 mL of water and 1 mL of 1N sodium hydroxide. The organic phase is dried over magnesium sulphate, filtered and then concentrated under reduced pressure to give 0.048 g of 3-[4-(2-hydroxy-1,1-dimethylethyl)phenyl]-5,5-dimethyl-1-{[2-(pyridin-3-ylamino)-pyridin-4-yl]methyl}imidazolidine-2,4-dione, the characteristics of which are as follows:

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue obtained
  3. concentrationThe solution is concentrated under reduced pressure
  4. customThe residue obtained
  5. customis purified by Preparative LC/MS (gradient: acetonitrile/water/TFA 0.07%)
  6. customThe product obtained
  7. dry with materialThe organic phase is dried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-73aec03e3b95491aa51738f14044dd51
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07935819B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes