Dimethylacetamide → HCID 86708519, Verbindung

HRID 921636Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 921636
Br[C:2]1[N:10]2[C:5]([C:6]([N:15]([CH:25]3[CH2:27][CH2:26]3)[CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[N:7][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[N:9]2)=[N:4][CH:3]=1.C[C:29]([N:31](C)C)=O>[C-]#N.[Zn+2].[C-]#N.[Zn].CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH:25]1([N:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[C:6]2[C:5]3=[N:4][CH:3]=[C:2]([C:29]#[N:31])[N:10]3[N:9]=[C:8]([S:11]([CH3:14])(=[O:13])=[O:12])[N:7]=2)[CH2:27][CH2:26]1

Komponenten

6

Edukt 2

HCID 31374DimethylacetamideHCID 899201847-bromo-N-cyclopropyl-N-(4-methoxybenzyl)-2-(methylsulfonyl)imidazo[2,1-f][1,2,4]triazin-4-amine

Produkt 1

HCID 86708519HCID 86708519, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 23994ZincKatalysatorHCID 178418851HCID 178418851, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In a round-bottom flask, a mixture of 7-bromo-N-cyclopropyl-N-(4-methoxybenzyl)-2-(methylsulfonyl)imidazo[2,1-f][1,2,4]triazin-4-amine (0.115 g, 0.254 mmol), zinc cyanide (0.021 g, 0.178 mmol), and zinc powder (4.99 mg, 0.076 mmol) in DMA (30 mL) was degassed by evacuating with vacuum and back filling with nitrogen. The mixture was treated with bis(tri-t-butylphosphine)palladium (0) (0.026 g, 0.051 mmol), degassed again as described above, and the reaction was heated at 100° C. for 4 hours. The reaction mixture was filtered and the filtrate diluted with ethyl acetate, washed with water, brine, dried with sodium sulfate and concentrated in vacuo. The crude product mixture was purified via ISCO (0-15% of methanol/dichloromethane in 20 minutes, 40 g silica column) to give the pure product 4-(cyclopropyl(4-methoxybenzyl)amino)-2-(methylsulfonyl)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (75 mg).

Aufarbeitung

  1. customwas degassed
  2. customby evacuating with vacuum
  3. customdegassed again
  4. filtrationThe reaction mixture was filtered
  5. additionthe filtrate diluted with ethyl acetate
  6. washwashed with water, brine
  7. dry with materialdried with sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe crude product mixture was purified via ISCO (0-15% of methanol/dichloromethane in 20 minutes, 40 g silica column)

Quellen und Nachweise

ORD-Eintrag
ord-97baf8d9155c4d2e84e8ca8f01839756
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273057B2

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