1-(4-Aminophenyl)-1H-pyridin-2-one → 5-chloro-thiophene-2-carboxylic acid ((R)-1-{2-[4-(2-oxo-pyridin-1-yl)-phenylamino]-acetyl}-pyrrolidin-3-yl)-amide

Participants

Reaction Steps

7.2 A solution of 250 mg 5-chloro-thiophene-2-carboxylic acid [(R)-1-(2-bromo-acetyl)-pyrrolidin-3-yl]-amide in 2 ml DMF was treated with 110 mg 1-(4-amino-phenyl)-1H-pyridin-2-one (CAS 13143-47-0), 0.12 ml TEA and 110 mg tetrabutylammonium iodide. The reaction mixture was stirred at r.t. for 2 days, then quenched with water and extracted with EtOAc. The organic layer was washed with water, dried over MgSO4 and filtrated. The crude product was purified by chromatography (silica gel; gradient: CH2Cl2 to CH2Cl2/MeOH 95:5) to give 72 mg 5-chloro-thiophene-2-carboxylic acid ((R)-1-{2-[4-(2-oxo-pyridin-1-yl)-phenylamino]-acetyl}-pyrrolidin-3-yl)-amide. MS 457.5 ([M+H]+)

Provenance & Evidence