Dimethylacetamide → N-[3-({2-[(2-chloropyrimidin-4-yl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]-3-methylpyridine-2-carboxamide

HRID 1874545Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1874545
[NH2:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([O:10][C:11]3[CH:12]=[C:13]([NH:17][C:18]([C:20]4[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][N:21]=4)=[O:19])[CH:14]=[CH:15][CH:16]=3)=[CH:6][N:5]2[CH:27]=1.[Cl:28][C:29]1[N:34]=[C:33](Cl)[CH:32]=[CH:31][N:30]=1.CN(C)C(=O)C>C(=O)([O-])O.[Na+]>[Cl:28][C:29]1[N:34]=[C:33]([NH:1][C:2]2[N:3]=[C:4]3[CH:9]=[CH:8][C:7]([O:10][C:11]4[CH:12]=[C:13]([NH:17][C:18]([C:20]5[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][N:21]=5)=[O:19])[CH:14]=[CH:15][CH:16]=4)=[CH:6][N:5]3[CH:27]=2)[CH:32]=[CH:31][N:30]=1

Komponenten

5

Edukt 3

HCID 31374DimethylacetamideHCID 775312,4-DichloropyrimidineHCID 57749390N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]phenyl}-3-methylpyridine-2-carboxamide

Produkt 1

HCID 57749228N-[3-({2-[(2-chloropyrimidin-4-yl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]-3-methylpyridine-2-carboxamideAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A mixture of N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]phenyl}-3-methylpyridine-2-carboxamide (150 mg, 0.417 mmol), 2,4-dichloropyrimidine (63.8 mg, 0.428 mmol) and N,N-dimethylacetamide (5 mL) was stirred at room temperature for 20 hr. The reaction mixture was diluted with aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH silica gel, 0%→100% ethyl acetate-hexane→2% methanol-ethyl acetate) to give the title compound (38.8 mg, 20%) as a white solid.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (NH silica gel, 0%→100% ethyl acetate-hexane→2% methanol-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-7d43d0f598a74e3986b6aa877ebd6bdd
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304557B2

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