Water → HCID 57626010, compound

HRID 546630Notes

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]

Participants

9

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 22038413Diborane dimethylsulfideHCID 57625974HCID 57625974, compound

Product 1

HCID 57626010HCID 57626010, compoundYield 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
Patent number
US07935819B2

Reaction notes

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