Water → 2-((2-Chloro-5-cyano-3-formylphenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

HRID 921764

Reaktionsgleichung

Reaktionsgleichung von HRID 921764
[Cl:1][C:2]1[C:7]([CH:8]=C)=[CH:6][C:5]([C:10]#[N:11])=[CH:4][C:3]=1[NH:12][C:13]1[N:18]=[C:17]([NH:19][CH:20]2[CH2:22][CH2:21]2)[C:16]2=[N:23][CH:24]=[C:25]([C:26]#[N:27])[N:15]2[N:14]=1.O.I([O-])(=O)(=O)=[O:30].[Na+]>CC(C)=O.CC(O)(C)C.[Os]>[Cl:1][C:2]1[C:7]([CH:8]=[O:30])=[CH:6][C:5]([C:10]#[N:11])=[CH:4][C:3]=1[NH:12][C:13]1[N:18]=[C:17]([NH:19][CH:20]2[CH2:22][CH2:21]2)[C:16]2=[N:23][CH:24]=[C:25]([C:26]#[N:27])[N:15]2[N:14]=1

Komponenten

7

Edukt 3

HCID 962Water2×HCID 23667635Sodium periodateHCID 867086492-((2-Chloro-5-cyano-3-vinylphenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

Produkt 1

HCID 867086482-((2-Chloro-5-cyano-3-formylphenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrileAusbeute 89,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23937OsmiumKatalysatorHCID 180AcetoneLösungsmittelHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

A suspension of 2-((2-chloro-5-cyano-3-vinylphenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (Example 399) (210 mg, 0.557 mmol) in acetone (50 mL) was heated to give a cloudy solution. After cooling to room temperature; water (5 mL), osmium tertroxide (0.350 mL, 2.5 wt % in t-BuOH, 0.028 mmol) and sodium periodate (262 mg, 1.23 mmol) were added. After overnight stirring, additional water (20 mL) was added and the reaction was left stirring for 1 day. Most of the acetone was removed and the suspended solid was collected by filtration, washed with water, and air dried to leave 2-((2-chloro-5-cyano-3-formylphenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (188 mg) as a light yellow solid.

Aufarbeitung

  1. temperaturewas heated
  2. customto give a cloudy solution
  3. waitthe reaction was left
  4. stirringstirring for 1 day
  5. customMost of the acetone was removed
  6. filtrationthe suspended solid was collected by filtration
  7. washwashed with water, and air
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f57cb42b4e73433a8f17b3f3114bd499
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273057B2

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