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Dimethylformamide → 6-cyano-N-[6-(3-{[3-(1-cyanocyclopropyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]nicotinamide

HRID 1668231
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1668231
Cl[C:2]1[CH:40]=[CH:39][C:5]([C:6]([NH:8][C:9]2[N:10]=[C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25](=[O:37])[C:26]5[CH:31]=[CH:30][CH:29]=[C:28]([C:32]6([C:35]#[N:36])[CH2:34][CH2:33]6)[CH:27]=5)[CH:19]=4)=[N:13][N:12]3[CH:38]=2)=[O:7])=[CH:4][N:3]=1.C(=O)([O-])O.[Na+].[CH3:46][N:47](C)C=O>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[C-]#N.[Zn+2].[C-]#N>[C:46]([C:2]1[CH:40]=[CH:39][C:5]([C:6]([NH:8][C:9]2[N:10]=[C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25](=[O:37])[C:26]5[CH:31]=[CH:30][CH:29]=[C:28]([C:32]6([C:35]#[N:36])[CH2:34][CH2:33]6)[CH:27]=5)[CH:19]=4)=[N:13][N:12]3[CH:38]=2)=[O:7])=[CH:4][N:3]=1)#[N:47]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 575057506-chloro-N-[6-(3-{[3-(1-cyanocyclopropyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]nicotinamide

Produkt 1

HCID 575057656-cyano-N-[6-(3-{[3-(1-cyanocyclopropyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]nicotinamideAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11186
Zinc cyanide (Zn(CN)2)
Katalysator
HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 6-chloro-N-[6-(3-{[3-(1-cyanocyclopropyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]nicotinamide (120 mg, 0.201 mmol), tetrakis(triphenylphosphine)palladium (0) (58 mg, 50.4 mol), zinc cyanide (26 mg, 0.225 mmol) and N,N-dimethylformamide (2.5 mL) was stirred with heating under an argon atmosphere at 100° C. for 6.5 hr. After the reaction mixture was allowed to cool to room temperature, saturated aqueous sodium hydrogencarbonate solution was added to the mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=50/50→100/0) to give the title compound (51 mg, 47%) as a yellow powder.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltrated
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=50/50→100/0)

Quellen und Nachweise

ORD-Eintrag
ord-bfbf321e660345a0ada580554f82162e
Quelldatensatz
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08044049B2

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