Ethanol → N-(5-(3,4-Difluorobenzylcarbamoyl)-2-fluorophenyl)-7-(6-(((2-hydroxy ethyl)(methyl)amino)methyl)pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

A suspension of N-(5-(3,4-difluorobenzylcarbamoyl)-2-fluorophenyl)-7-(6-formylpyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide (step 1) (100 mg, 0.189 mmol), 2-(methylamino)ethanol (70.9 mg, 0.944 mmol) and molecular sieves in EtOH (2 ml) was heated at 70° C. overnight. The mixture was cooled to 0° C. and treated with sodium borohydride (7.15 mg, 0.189 mmol). The mixture was allowed to warm to RT and was stirred overnight. The resulting suspension was removed by filtration and the filtrate was concentrated in vacuo. The residue was partitioned between EtOAc and water. The organic portion was separated, washed with NaHCO3, dried (MgSO4) and concentrated in vacuo. Purification of the residue by preparative chromatography eluting with 25-50% 0.1% TFA acetonitrile/water afforded fractions that were combined and diluted with NaHCO3 and 5% trifluoroethanol/DCM. The organics were separated, dried and concentrated in vacuo to afford a white solid. The solid was triturated with EtOH/Ether to afford the title compound as a white solid;

Provenance & Evidence