Triethylamine hydrochloride → HCID 86760800, compound

Participants

Reaction Conditions

Reaction Steps

Heat at 120° C. a mixture of (+/−)-cis-4-[(3,5-bis-trifluoromethyl-benzyl)-cyano-amino]-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid isopropyl ester (100 mg, 0.184 mmol), sodium azide (17 mg, 0.258 mmol) and triethyl amine hydrochloride (35 mg, 0.258 mmol) in dry toluene under an atmosphere of nitrogen for 8 h. Then add more sodium azide (6 mg) and triethyl amine hydrochloride (13 mg) and heat the mixture for 4 h. Cool to room temperature, dilute with ethyl acetate, and wash with 1 N HCl. Dry the organic layer over anhydrous sodium sulfate, filter, and remove the solvent under reduced pressure. Purify the residue by flash chromatography, eluting with hexanes/ethyl acetate, to afford the title compound (61 mg, 50%). MS (ES+): 588 (M+H).

Provenance & Evidence