Nitrogen → HCID 67212646, compound

Participants

Reaction Steps

(5-{2-[(N-Benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-6-methoxy-pyridin-3-yl)-acetic acid ethyl ester (0.700 g, 1.3 mmol), ammonium formate (0.164 g, 2.6 mmol), and palladium on carbon (10%; 0.138 g) were combined in an evacuated flask that was backfilled with N2. MeOH (10 mL) was added, and the resulting suspension was stirred at room temperature for 3 hours. A balloon of H2 was added, and the reaction was stirred under an atmosphere of H2 overnight at room temperature. The mixture was filtered through Celite, and the filtrate was concentrated. The residue was dissolved in EtOAc and washed with H2O and brine, and then dried over Na2SO4, filtered, and concentrated. The crude material was purified by silica gel chromatography (0-5% MeOH in CH2Cl2) to give [5-(2-ethylaminomethyl-4-trifluoromethyl-phenyl)-6-methoxy-pyridin-3-yl]-acetic acid ethyl ester, which was subsequently reacted with acetyl chloride as described in Example 5, Step 4 to provide (5-{2-[(N-acetyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-6-methoxy-pyridin-3-yl)-acetic acid ethyl ester. The ester was hydrolyzed to the acid as described in Example 3, Step 7.

Provenance & Evidence