Trifluoroacetic acid → (+/-)-2-((2-chloro-5-cyano-3-((4aR,8aR)-hexahydro-1H-pyrido[3,4-b][1,4]oxazin-6(7H)-yl)phenyl)amino)-4-(ethylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

HRID 1430911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1430911
[Cl:1][C:2]1[C:7]([NH:8][C:9]2[N:14]=[C:13]([N:15](CC)[CH2:16][C:17]3C=CC(OC)=CC=3)[C:12]3=[N:27][CH:28]=[C:29]([C:30]#[N:31])[N:11]3[N:10]=2)=[CH:6][C:5]([C:32]#[N:33])=[CH:4][C:3]=1[N:34]1[CH2:43][CH2:42][C@@H:41]2[C@H:36]([O:37][CH2:38][CH2:39][N:40]2C(OC(C)(C)C)=O)[CH2:35]1.C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>ClCCCl>[Cl:1][C:2]1[C:3]([N:34]2[CH2:43][CH2:42][C@@H:41]3[C@H:36]([O:37][CH2:38][CH2:39][NH:40]3)[CH2:35]2)=[CH:4][C:5]([C:32]#[N:33])=[CH:6][C:7]=1[NH:8][C:9]1[N:14]=[C:13]([NH:15][CH2:16][CH3:17])[C:12]2=[N:27][CH:28]=[C:29]([C:30]#[N:31])[N:11]2[N:10]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 86708617(+/-)-(4aR,8aR)-tert-butyl 6-(2-chloro-5-cyano-3-((7-cyano-4-(ethyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)octahydro-1H-pyrido[3,4-b][1,4]oxazine-1-carboxylate

Produkt 1

HCID 86708616(+/-)-2-((2-chloro-5-cyano-3-((4aR,8aR)-hexahydro-1H-pyrido[3,4-b][1,4]oxazin-6(7H)-yl)phenyl)amino)-4-(ethylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrileAusbeute 76,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

(+/−)-(4aR,8aR)-tert-butyl 6-(2-chloro-5-cyano-3-((7-cyano-4-(ethyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)octahydro-1H-pyrido[3,4-b][1,4]oxazine-1-carboxylate (75 mg, 0.104 mmol) was taken up in DCE (2 mL), anisole (0.05 mL, 0.458 mmol) and TFA (0.5 mL, 6.49 mmol). The mixture stirred 2 h at 25° C. and solvents removed. 50 ml 2N NH3/MeOH was added and stirred for 30 mins. The white precipitate was collected by filtration and washed with 20 ml cold MeOH, then ether and dried under air-suction for 2 hrs to give (+/−)-2-((2-chloro-5-cyano-3-((4aR,8aR)-hexahydro-1H-pyrido[3,4-b][1,4]oxazin-6(7H)-yl)phenyl)amino)-4-(ethylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (38 mg).

Aufarbeitung

  1. customsolvents removed
  2. addition50 ml 2N NH3/MeOH was added
  3. stirringstirred for 30 mins
  4. filtrationThe white precipitate was collected by filtration
  5. washwashed with 20 ml cold MeOH
  6. dry with materialether and dried under air-suction for 2 hrs

Quellen und Nachweise

ORD-Eintrag
ord-4cfb614c45584cfdb60b775eeb469ac1
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940736B2

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