7-bromo-2-chloro-N-ethyl-N-(4-methoxybenzyl)imidazo[2,1-f][1,2,4]triazin-4-amine → 2-Chloro-4-(ethyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

HRID 921623Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 921623
Br[C:2]1[N:10]2[C:5]([C:6]([N:12]([CH2:22][CH3:23])[CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)=[N:7][C:8]([Cl:11])=[N:9]2)=[N:4][CH:3]=1.[Cu][C:25]#[N:26]>CN1C(=O)CCC1>[Cl:11][C:8]1[N:7]=[C:6]([N:12]([CH2:22][CH3:23])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:5]2=[N:4][CH:3]=[C:2]([C:25]#[N:26])[N:10]2[N:9]=1

Komponenten

4

Edukt 2

HCID 867084717-bromo-2-chloro-N-ethyl-N-(4-methoxybenzyl)imidazo[2,1-f][1,2,4]triazin-4-amineHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 867084732-Chloro-4-(ethyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrileAusbeute 101,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To an oven dried 500 ml round bottom flask was added 7-bromo-2-chloro-N-ethyl-N-(4-methoxybenzyl)imidazo[2,1-f][1,2,4]triazin-4-amine (12.5 g, 31.5 mmol) and copper(I) cyanide (9.0 g, 100 mmol). The flask was caped under nitrogen and NMP (250 mL) was added. The mixture stirred 5 min at 25° C. and the flask was evacuated and back-filled with nitrogen 3×. The reaction stirred at 135° C. (oil bath) 21 hr. The reaction cooled to 25° C., diluted with ethyl acetate (500 ml) and filter through celite bed. The bed was washed with EtOAc 3×100 ml and the filtrate washed with water 1×300 ml and brine 3×150 ml. The organics dried with sodium sulphate and remove solvent. The material was crystallized from IPA and filtered to afford 2-chloro-4-(ethyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (11 g).

Aufarbeitung

  1. customTo an oven dried 500 ml round bottom flask
  2. customThe flask was caped under nitrogen
  3. customthe flask was evacuated
  4. additionback-filled with nitrogen 3×
  5. stirringThe reaction stirred at 135° C. (oil bath) 21 hr
  6. temperatureThe reaction cooled to 25° C.
  7. additiondiluted with ethyl acetate (500 ml)
  8. filtrationfilter through celite bed
  9. washThe bed was washed with EtOAc 3×100 ml
  10. washthe filtrate washed with water 1×300 ml and brine 3×150 ml
  11. dry with materialThe organics dried with sodium sulphate
  12. customremove solvent
  13. customThe material was crystallized from IPA
  14. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-5b1d8744985844eb9e64075d9f390969
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273057B2

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