Tetrahydrofuran → N-[5-(5-Cyanopyridin-3-ylethynyl)-2-fluorophenyl]-isobutyramide

HRID 606921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 606921
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][C:11]2[CH:12]=[N:13][CH:14]=[C:15]([CH:18]=2)[C:16]#[N:17])[CH:5]=[CH:6][C:7]=1[F:8].[C:19](OCC)(=O)C.[O:25]1[CH2:29][CH2:28][CH2:27]C1>>[C:16]([C:15]1[CH:18]=[C:11]([C:10]#[C:9][C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([NH:1][C:29](=[O:25])[CH:28]([CH3:19])[CH3:27])[CH:3]=2)[CH:12]=[N:13][CH:14]=1)#[N:17]

Komponenten

4

Edukt 3

HCID 8028Tetrahydrofuran2×HCID 8857Ethyl AcetateHCID 670478225-(3-Amino-4-fluorophenylethynyl)-nicotinonitrile

Produkt 1

HCID 67047872N-[5-(5-Cyanopyridin-3-ylethynyl)-2-fluorophenyl]-isobutyramideAusbeute 84 %

Versuchsvorschrift

Add a solution of isobutynyl chloride (0.09 g, 1.08 mmol) dissolved in tetrahydrofuran to a solution of 5-(3-amino-4-fluorophenylethynyl) -nicotinonitrile, (prepared as described in EXAMPLE 160), (0.2 g, 0.8 mmol) in anhydrous tetrahydrofuran and stir overnight at room temperature. Pour into ethyl acetate, wash with water and an aqueous saturated solution of sodium chloride, dry (potassium carbonate), filter and concentrate. Purify the residue by silica gel chromatography, eluting with 100:0 to 95:5 dichloromethane:ethyl acetate, to give the title compound as a white solid (210 mg, 84%).

Aufarbeitung

  1. washwash with water
  2. dry with materialan aqueous saturated solution of sodium chloride, dry (potassium carbonate)
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the residue by silica gel chromatography
  6. washeluting with 100:0 to 95:5 dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-2e81bec6aa2e4ab89ae75b6cede69755
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915424B2

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