Diisopropylethylamine → 6-{5-[(4,4-Difluorocyclohexylamino)methyl]naphthalen-1-yloxy}-nicotinamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-(5-formylnaphthalen-1-yloxy)nicotinamide (Preparation 35) (200 mg, 0.7 mmol) in MeOH (10 mL) was added 4,4-difluorocyclohexylammonium chloride (141 mg, 0.8 mmol), DIPEA (358 μl, 2.1 mmol) and 4 Å molecular sieves (200 mg). The mixture was stirred at 50° C. for 16 h, cooled to rt and NaBH4 (78 mg, 2.1 mmol) added. After 3 h water (1 mL) was added and the mixture filtered. Solvent was removed in vacuo and the residue purified by column chromatography (10% MeOH-EtOAc) to give the title compound: RT=2.40 min; m/z (ES+)=412.2 [M+H]+.

Provenance & Evidence