Iodoacetamide → HCID 22064661, compound

Participants

Reaction Steps

To a stirred solution of (RS)-N-(4-cyano-benzyl)-2-ethoxy-2-[3-(2-hydroxy-phenyl)-4-methyl-pyrazol-1-yl]-acetamide (200 mg) at r.t. in DMF (4 ml) under an argon atmosphere were added cesium carbonate (200 mg) followed by iodoacetamide (114 mg). The mixture was then stirred for 2 h. The mixture was diluted with EtOAc and water. The aqueous phase was extracted with EtOAc. The combined organics were washed with water. A solid started to precipitate out of the organic phase in the separating funnel. This solid was collected by filtration and washed with cyclohexane to give (RS)-2-[3-(2-carbamoylmethoxy-phenyl)-4-methyl-pyrazol-1-yl]-N-(4-cyano-benzyl)-2-ethoxy-acetamide (153 mg) as white powder. The organic layer of the filtrate was separated and washed with brine, dried (MgSO4), filtered and concentrated to leave a yellow solid. This was taken in Et2O (5 ml) and 5 drops of methanol were added. The suspension was stirred for 30 min at r.t. and this second crop of product was collected by filtration, washed with Et2O and dried to give more (RS)-2-[3-(2-carbamoylmethoxy-phenyl)-4-methyl-pyrazol-1-yl]-N-(4-cyano-benzyl)-2-ethoxy-acetamide (31 mg) of an off-white powder. MS 448.5 ([M+H]+)

Provenance & Evidence