Triethylamine → HCID 86613803, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[(3,5-bis-trifluoromethyl-benzyl)-cyano-amino]-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid isopropyl ester (from Example 9) (250 mg, 0.429 mmol) in EtOH (2.6 mL), add hydroxylamine hydrochloride (75 mg, 1.07 mmol) and triethylamine (0.150 mL, 1.07 mmol) at room temperature. Stir the reaction mixture at 80° C. overnight. Cool the mixture and remove the solvents under reduced pressure. Dilute the residue with ethyl acetate and add brine. Separate the layers, dry the organic phase over magnesium sulfate, filter, and concentrate in vacuo. Purify the residue by flash chromatography, eluting with hexanes/ethyl acetate, to afford the title compound (84 mg, 32%). MS (ES+): 616 (M+H).

Provenance & Evidence