Ammonium Hydroxide → 5-Bromo-1-(4-cyano-benzyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide

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Reaction Steps

A solution of 5-bromo-1-(4-cyano-benzyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (preparation 1c, 1.00 g, 2.88 mmol), TBTU (0.925 g, 2.88 mmol), DIPEA (1.50 mL, 8.67 mmol) in DMF (7 mL) is stirred for 30 min. Then, 4-(methylsulfonyl)benzylamine hydrochloride (0.766 g, 3.46 mmol) is added and the reaction mixture is stirred for 18 h at room temperature. The reaction mixture is diluted with MeOH, basified with NH4OH, filtered and purified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.3% NH4OH, 60° C.). Yield: 0.66 g (29% of theory); ESI mass spectrum: [M+H]+=514 (bromine isotope pattern); Retention time HPLC: 0.88 min (Z003—001).

Provenance & Evidence