Sodium Bicarbonate → N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-fluorophenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 1663777

Reaktionsgleichung

Reaktionsgleichung von HRID 1663777
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[F:24])[O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[N:14]=2)[N:11]=1.[CH3:25][N:26]1[C:30]([C:31](Cl)=[O:32])=[CH:29][C:28]([CH3:34])=[N:27]1.C(=O)([O-])O.[Na+]>CN(C)C(=O)C>[CH:18]1([C:16]([NH:15][C:13]2[N:14]=[C:9]3[CH:8]=[CH:7][C:6]([O:5][C:4]4[CH:21]=[CH:22][C:23]([F:24])=[C:2]([NH:1][C:31]([C:30]5[N:26]([CH3:25])[N:27]=[C:28]([CH3:34])[CH:29]=5)=[O:32])[CH:3]=4)=[N:11][N:10]3[CH:12]=2)=[O:17])[CH2:20][CH2:19]1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 27362992,5-Dimethyl-2H-pyrazole-3-carbonyl chlorideHCID 57505446N-[6-(3-amino-4-fluorophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide

Produkt 1

HCID 24767979N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-fluorophenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamideAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel2×

Versuchsvorschrift

To a solution of N-[6-(3-amino-4-fluorophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (100 mg, 0.306 mmol) in N,N-dimethylacetamide (4.0 mL) was added a solution of 1,3-dimethyl-1H-pyrazole-5-carbonyl chloride (51 mg, 0.321 mmol) in N,N-dimethylacetamide (1.0 mL) under ice-cooling, and the mixture was stirred at room temperature for 30 min. Under ice-cooling, aqueous sodium hydrogencarbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate, 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 (methanol/ethyl acetate=0/100→5/95) and recrystallized from methanol/ethyl acetate to give the title compound (88.8 mg, 65%) as pale-yellow crystals. melting point 237° C.

Aufarbeitung

  1. temperaturecooling
  2. temperatureUnder ice-cooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltrated
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→5/95)
  9. customrecrystallized from methanol/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-9cce0a6c81064b25bf0cd02d5fcb9bcc
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08034812B2

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