Acetone → 4-(5-((2-Cyanopropan-2-yl)amino)pyridin-2-yl)butanenitrile

HRID 1504966Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1504966
[Si]([C:5]#[N:6])(C)(C)C.[NH2:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][C:17]#[N:18])=[N:12][CH:13]=1.[CH3:19][C:20]([CH3:22])=O>[Cl-].[Cl-].[Zn+2]>[C:5]([C:20]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][C:17]#[N:18])=[N:12][CH:13]=1)([CH3:22])[CH3:19])#[N:6]

Komponenten

5

Edukt 3

HCID 180AcetoneHCID 82115Trimethylsilyl cyanideHCID 682926344-(5-Aminopyridin-2-yl)butanenitrile

Produkt 1

HCID 682923294-(5-((2-Cyanopropan-2-yl)amino)pyridin-2-yl)butanenitrileAusbeute 102,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3007855ZincchlorideKatalysator

Versuchsvorschrift

TMSCN (0.24 mL, 1.8 mmol) was added to a mixture of compound 78 (100 mg, 0.6 mmol), acetone (0.27 mL, 3.6 mmol) and ZnCl2 (10 mg, 0.08 mmol) with stirring. The reaction mixture was stirred at room temperature for 1 h and concentrated in vacuo. The residue was diluted with water and extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated to dryness to give compound 79 (140 mg, 98%) as a light yellow oil. The crude product was used directly for the next step without purification. 1H NMR (400 MHz, CDCl3) δ8.12 (s, 1H), 7.20-7.25 (m, 1H), 7.00-7.06 (m, 1H), 2.81 (t, 2H, J=7.1 Hz). 2.32 (t, 2H, J=7.1 Hz), 1.98-2.12 (m, 2H), 1.69 (s, 6H).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at room temperature for 1 h
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with DCM
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-6467590991534c90b83ac867d375a4e5
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216957B2

Notizen zur Reaktion

Wird geladen…