Reaktion #166595

Reaktionsgleichung

Hydrogen chloride

N-(1-((1H-pyrazol-4-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

cesium hydroxide hydrate

bromoethane

→

N-(3-ethyl-1-((1-ethyl-1H-pyrazol-4-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide dihydrochloride

Ausbeute 19.8%

Lösungsmittel

N,N-dimethyl formamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe mixture was filtered
2. 2
   Waschenwashed with methanol and ethyl acetate
3. 3
   Einengenconcentrated under a stream of nitrogen
4. 4
   SonstigeThe material was purified
5. 5
   Wascheneluting with 10% methanol in dichloromethane
6. 6
   workup.DISSOLUTIONThe isolated product was dissolved in a mixture of dichloromethane and methanol
7. 7
   SonstigeRemoval of the solvent under reduced pressure

Vorschrift

To a solution of N-(1-((1H-pyrazol-4-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (20 mg, 0.052 mmol; prepared according to Example 21, Step A) in dry N,N-dimethyl formamide (0.5 mL) was added cesium hydroxide hydrate (8.7 mg, 0.052 mmol) and bromoethane (5.7 mg, 0.052 mmol). The mixture was stirred under a nitrogen atmosphere for 60 minutes at ambient temperature. The mixture was filtered, washed with methanol and ethyl acetate, and concentrated under a stream of nitrogen. The material was purified using preparative thin layer chromatography on silica, eluting with 10% methanol in dichloromethane. The isolated product was dissolved in a mixture of dichloromethane and methanol. Hydrogen chloride (0.5 mmol; 2M solution in diethyl ether) was added. Removal of the solvent under reduced pressure followed by high vacuum gave N-(3-ethyl-1-((1-ethyl-1H-pyrazol-4-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide dihydrochloride (5.0 mg). MS (APCI), positive scan, m/z=414.2 (M+H).

Quelle