Sodium Bicarbonate → HCID 71269976, Verbindung

HRID 1626924

Reaktionsgleichung

Reaktionsgleichung von HRID 1626924
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]([C:11]2[N:12]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:13](=[O:22])[C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])[CH3:10])[C:5](C#N)=[CH:4][N:3]=1.[C:31]([O-:34])(O)=[O:32].[Na+]>O1CCOCC1.S(=O)(=O)(O)O.O>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]([C:11]2[N:12]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:13](=[O:22])[C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])[CH3:10])[C:5]([C:31]([OH:34])=[O:32])=[CH:4][N:3]=1

Komponenten

5

Edukt 2

HCID 516892Sodium BicarbonateHCID 67950671(S)-2-amino-4-((1-(8-chloro-1-oxo-2-phenyl-1,2-dihydroisoquinolin-3-yl)ethyl)amino)pyrimidine-5-carbonitrile

Produkt 1

HCID 71269976HCID 71269976, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 312751,4-DioxaneLösungsmittelHCID 21910475Sulfuric acid hydrate (1:1)Lösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of (S)-2-amino-4-((1-(8-chloro-1-oxo-2-phenyl-1,2-dihydroisoquinolin-3-yl)ethyl)amino)pyrimidine-5-carbonitrile (53) (495 mg, 1.19 mmol) in anhydrous 1,4-dioxane (20 mL), sulfuric acid/water (1:1, 7 mL) was added dropwise. The reaction mixture was stirred at 90° C. for 60 h. The mixture was allowed to cool to RT and basified with NaHCO3. The precipitate was collected by filtration and then dissolved in water. The resulting mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to afford the product 117, (S)-2-amino-4-((1-(8-chloro-1-oxo-2-phenyl-1,2-dihydroisoquinolin-3-yl)ethyl)amino)pyrimidine-5-carboxylic acid. The material was used directly in the next step.

Aufarbeitung

  1. filtrationThe precipitate was collected by filtration
  2. dissolutiondissolved in water
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-455e6f35f803470689cc75807c6672c8
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785470B2

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