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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
ノート
印刷プレビュー

反応式

HRID 546630 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 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

生成物 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
収率 45%

試薬・触媒・溶媒 4

HCID 313Hydrochloric Acid溶媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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:

後処理

  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

出典と根拠

ORDレコード
ord-73aec03e3b95491aa51738f14044dd51
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07935819B2

反応ノート

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