Hydrochloric Acid → HCID 178463673, compound

Participants

Reaction Steps

(3,5-Bis-trifluoromethyl-benzyl)-[2-(cyclopentylmethyl-ethyl-amino)-quinolin-4-yl]-cyanamide (0.368 g, 0.689 mmol), sodium azide (0.049 g, 0.758 mmol), and zinc bromide (0.155 g, 0.689 mmol) were added to a round bottom flask under a N2 atmosphere. To this reaction mixture, water (8 mL) was added, and the resulting mixture was refluxed for 24 h with vigorous stirring. Afterwards, the reaction mixture was cooled to RT and a mixture of HCl (3N, 0.92 mL) and ethyl acetate was added. The vigorous stirring was continued until no solid was separated out and the aqueous layer had reached a pH of 1. The organic layer was separated and concentrated under vacuum. A solution of sodium hydroxide (0.25 N, 6.25 mL) was added to the residue and was stirred for 30 minutes until the residue was dissolved, and a suspension of zinc hydroxide was formed. The suspension was filtered and washed with NaOH (1N), and the filtrate was acidified with 3N HCl dropwise to afford (3-{[(3,5-bis-trifluoromethyl-benzyl)-(1H-tetrazol-5-yl)-amino]-methyl}-quinolin-2-yl)-cyclopentylmethyl-ethyl-amine as a yellow solid (0.140 g), yield: 35%.

Provenance & Evidence