Cyanogen Bromide → HCID 178508227, compound

Participants

Reaction Steps

To a solution of 4-(S),N-dicyclohexy-4-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-N-(1H-tetrazol-5-ylmethyl)-butyramide (0.75 g, 1.3 mmole) in ethanol (30 mL) and THF (20 mL) was added palladium on carbon (10%, 0.48 g). The reaction mixture was hydrogenated for 1 hour at 20 psi. The reaction mixture was then filtered. Cyanogen bromide (3 M in dichloromethane, 0.65 ml, 1.9 mmole) was added, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated and the resulting residue was purified by reverse phase HPLC to yield 4-{[4-(2-amino-6-phenoxy-4H-pyrido[3,4-d]pyrimidin-3-yl)-4-(S),N-dicyclohexyl-N-(1H-tetrazol-5-ylmethyl)-butyramide as a white solid, as its corresponding TFA salt.

Provenance & Evidence