Water → (S)-N-(3-(2-(Dimethylamino)ethoxy)-5-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl)methanesulfonamide

HRID 1052753

Reaktionsgleichung

Reaktionsgleichung von HRID 1052753
[OH:1][C:2]1[CH:3]=[C:4]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[CH:5]=[C:6]([C:8]2[C:16]3[C:15]([NH:17][C@H:18]([C:20]4[N:25]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[C:24](=[O:32])[C:23]5=[C:33]([CH3:36])[CH:34]=[CH:35][N:22]5[N:21]=4)[CH3:19])=[N:14][CH:13]=[N:12][C:11]=3[NH:10][CH:9]=2)[CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].Cl[CH2:50][CH2:51][NH+:52]([CH3:54])[CH3:53].O>CN(C)C=O>[CH3:53][N:52]([CH3:54])[CH2:51][CH2:50][O:1][C:2]1[CH:3]=[C:4]([NH:37][S:38]([CH3:41])(=[O:39])=[O:40])[CH:5]=[C:6]([C:8]2[C:16]3[C:15]([NH:17][C@H:18]([C:20]4[N:25]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[C:24](=[O:32])[C:23]5=[C:33]([CH3:36])[CH:34]=[CH:35][N:22]5[N:21]=4)[CH3:19])=[N:14][CH:13]=[N:12][C:11]=3[NH:10][CH:9]=2)[CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 20717(2-Chloroethyl)dimethylamine, chlorideHCID 901023362,3-d]Pyrimidin-5-yl]-5-oxidanyl-phenyl]methanesulfonamide

Produkt 1

HCID 90102856(S)-N-(3-(2-(Dimethylamino)ethoxy)-5-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl)methanesulfonamideAusbeute 62,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

(S)—N-(3-Hydroxy-5-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl)methanesulfonamide (6 mg, 0.01 mmol) was dissolved in 120 μl N,N-dimethylformamide. Sodium carbonate (8 mg, 0.07 mmol) and 2-chloro-N,N-dimethylethanaminium chloride (4 mg, 0.03 mmol) were added and the mixture was stirred at 50° C. overnight. The reaction was poured into water and extracted twice with ethyl acetate. The organics were combined and washed with brine, dried over sodium sulphate, filtered and evaporated under reduced pressure. The residue was purified using SP1® Purification System (0% to 100%, dichloromethane-dichloromethane/2-propanol 85:15) to give 4 mg (56% yield) of the title compound.

Aufarbeitung

  1. extractionextracted twice with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified
  7. customSP1® Purification System (0% to 100%, dichloromethane-dichloromethane/2-propanol 85:15)

Quellen und Nachweise

ORD-Eintrag
ord-3519fe54de6640d488dbb0549ce9a981
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388189B2

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