4-Ethyl-3-thiosemicarbazide → (S)-2-(1-((5-(5-(Ethylamino)-1,3,4-thiadiazol-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052756Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1052756
[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)=[CH:28][NH:27][C:23]=3[N:24]=[CH:25][N:26]=1)[CH3:19])=[N:6]2.[CH2:33]([NH:35][C:36]([NH:38][NH2:39])=[S:37])[CH3:34].O(Cl)Cl.[P+5]>O1CCOCC1>[CH2:33]([NH:35][C:36]1[S:37][C:30]([C:29]2[C:22]3[C:21]([NH:20][C@H:18]([C:7]4[N:8]([C:12]5[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=5)[C:9](=[O:11])[C:10]5=[C:2]([CH3:1])[CH:3]=[CH:4][N:5]5[N:6]=4)[CH3:19])=[N:26][CH:25]=[N:24][C:23]=3[NH:27][CH:28]=2)=[N:39][N:38]=1)[CH3:34]

Komponenten

5

Edukt 3

HCID 15517804-Ethyl-3-thiosemicarbazideHCID 90102798HCID 90102798, VerbindungHCID 178479711HCID 178479711, Verbindung

Produkt 1

HCID 136929378(S)-2-(1-((5-(5-(Ethylamino)-1,3,4-thiadiazol-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a suspension of (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 (50 mg, 0.12 mmol) and N-ethylhydrazinecarbothioamide (21 mg, 0.18 mmol) in 1 ml 1,4-dioxane was added phosphorus (V) oxychloride (12.5 μL, 0.13 mmol). The mixture was stirred at 80° C. overnight. The solvent was evaporated and the residue was poured into water and ethyl acetate. The mixture was basified to pH 10 with sodium carbonate and extracted twice with ethyl acetate. The organics were combined and washed with water, brine, dried over sodium sulphate, filtered and evaporated under reduced pressure. The residue was precipitated using diethyl ether, filtered, washed with cold diethyl ether and dried in a vacuum oven to obtain 14 mg (29% yield) of the title compound.

Aufarbeitung

  1. customThe solvent was evaporated
  2. additionthe residue was poured into water and ethyl acetate
  3. extractionextracted twice with ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was precipitated
  9. filtrationfiltered
  10. washwashed with cold diethyl ether
  11. customdried in a vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-b9eaa6a7dc594a07b816f44cd88535e3
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388189B2

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