Hydrochloric Acid → HCID 11202388, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of N-(2,6-dichloro-5-quinolinyl)-cyclohexaneacetamide (Example 1 (a)) (170 mg) and potassium carbonate (350 mg) in N-methylpyrrolidinone (4 mL) was added 2-[(2-aminoethyl)amino]-ethanol (500 μL). The mixture was heated at 120° C. for 5 hours after which it was cooled and poured into water. The resulting solid was isolated by filtration, dried and suspended in dichloromethane (5 mL). The suspension was then treated with di-tert-butyl dicarbonate (220 mg) and triethylamine (200 μL) and stirred for 2 hours. The mixture was poured into water and extracted with dichloromethane (3×20 mL). The combined organic layers were dried, filtered and concentrated. Purification (SiO2, methanol:dichloromethane solution 2.5:97.5 as eluant) yielded the desired isomer which was then dissolved in dichloromethane (5 mL) and methanol (0.5 mL), and treated with hydrochloric acid in 1,4-dioxane (4M, 1 mL) for 1 hour. The resultant suspension was evaporated to dryness and recrystallised from methanol/ethyl acetate to give the title compound as a colourless solid (65 mg).

Provenance & Evidence