Reaktion #166596

Reaktionsgleichung

Hydrogen chloride

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

(bromomethyl)cyclopropane

cesium hydroxide hydrate

→

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

Ausbeute 21.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe mixture was filtered
2. 2
   Waschenwashed with methanol and ethyl acetate
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   SonstigeThe residue was purified
5. 5
   Wascheneluting with 10% methanol in dichloromethane
6. 6
   workup.DISSOLUTIONThe product was dissolved in a mixture of dichloromethane and methanol
7. 7
   Sonstigethe solvent was removed 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 DMF (0.5 mL) was added (bromomethyl)cyclopropane (7.0 mg, 0.052 mmol) and cesium hydroxide hydrate (8.7 mg, 0.052 mmol). The mixture was stirred at ambient temperature for 60 minutes. The mixture was filtered, washed with methanol and ethyl acetate, and concentrated under reduced pressure. The residue was purified using preparative thin layer chromatography on silica, eluting with 10% methanol in dichloromethane. The product was dissolved in a mixture of dichloromethane and methanol. Hydrogen chloride (0.52 mmol; 2M solution in diethyl ether) was added and the solvent was removed under reduced pressure, followed by high vacuum to give N-(1-((1-(cyclopropylmethyl)-1H-pyrazol-4-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide dihydrochloride (5.6 mg). MS (APCI), positive scan, m/z=440.2 (M+H).

Quelle