Benzylamine → (S)-N-Benzyl-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]pyrimidine-5-carboxamide

HRID 1052717Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1052717
[CH3:1][C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[C:9](=[O:11])[N:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:7]([C@@H:18]([NH:20][C:21]1[C:22]3[C:29]([C:30](O)=[O:31])=[CH:28][NH:27][C:23]=3[N:24]=[CH:25][N:26]=1)[CH3:19])=[N:6]2.[CH2:33]([NH2:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(N(C(C)C)CC)(C)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CN(C=O)C>[CH2:33]([NH:40][C:30]([C:29]1[C:22]2[C:21]([NH:20][C@H:18]([C:7]3[N:8]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:9](=[O:11])[C:10]4=[C:2]([CH3:1])[CH:3]=[CH:4][N:5]4[N:6]=3)[CH3:19])=[N:26][CH:25]=[N:24][C:23]=2[NH:27][CH:28]=1)=[O:31])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Komponenten

6

Edukt 4

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 90102798HCID 90102798, Verbindung

Produkt 1

HCID 73775108(S)-N-Benzyl-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]pyrimidine-5-carboxamideAusbeute 46,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

(S)-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]pyrimidine-5-carboxylic acid (30 mg, 0.07 mmol), benzylamine (20 mg, 0.19 mmol) and diisopropylethylamine (50 μl, 0.29 mmol) were dissolved in DMF (1.5 ml) and stirred for 30 min. The reaction flask was then sealed and T3P® (50% in DMF, 50 μl) was added dropwise and the reaction mixture was stirred overnight at room temperature. The mixture was poured into ice-water and extracted with ethyl acetate. The resulting organic solution was washed with water and brine, dried over magnesium sulphate, filtered and the solvents were removed under reduced pressure. The product was purified by flash chromatography (0% to 5% DCM/MeOH) to give 17 mg (46% yield) of the title compound as a white solid.

Aufarbeitung

  1. customThe reaction flask was then sealed
  2. stirringthe reaction mixture was stirred overnight at room temperature
  3. extractionextracted with ethyl acetate
  4. washThe resulting organic solution was washed with water and brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure
  8. customThe product was purified by flash chromatography (0% to 5% DCM/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-08684804f58646e590a41fc0c12a6bfe
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388189B2

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