Borohydride → 6-(5-{[(2,2-Dimethylcyclopropylmethyl)amino]methyl]naphthalene-1-yloxy}nicotinamide

Participants

Reaction Steps

To a solution of 6-(5-formylnaphthalen-1-yloxy)nicotinamide (Preparation 35) (200 mg, 0.68 mmol) and (2,2-dimethylcyclopropyl)methylamine hydrochloride (111 mg, 0.82 mmol) in a 1:1 mixture of MeOH/DCM (12 mL) was added PS-diisopropylethylamine (3.66 mmol/g, 374 mg, 1.37 mmol) and the reaction was stirred at rt for 16 h. PS-borohydride (2 mmol/g, 1.03 g, 2.05 mmol) was added and the reaction was stirred for 30 min Water (0.5 mL) was added and the mixture purified through an SCX column (10 g/70 mL) eluting with 1% NH4OH in MeOH. Solvent was removed in vacuo and the residue was triturated with EtOAc to give the title compound: RT=2.60 min; m/z (ES+)=376.2 [M+H]+.

Provenance & Evidence