12-Aminododecanoic Acid → HCID 178512403, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 12-aminododecanoic acid (1) (0.096 g, 0.45 mmol) and diisopropylethylamine (0.39 mL, 2.23 mmol) in absolute ethanol (5 mL) was stirred at 70° C. for 30 min. 1-(3,5-Diamino-6-chloropyrazine-2-carbonyl)-2-methylisothiourea hydriodide (191 mg, 0.49 mmol) was added in one portion and heating at 70° C. was continued for a further 16 hours. After this time, the reaction was cooled to room and the resulting yellow precipitate collected by filtration and washed with ethanol (2×2 mL). Further purification by Biotage silica gel column chromatography using a gradient of 3% to 20% of 10% concentrated aqueous ammonium hydroxide in methanol to dichloromethane afforded acid 2 (96 mg, 50%) as a yellow solid: 1H NMR (500 MHz, DMSO-d6) δ 1.25 (m, 14H), 1.50 (m, 4H), 2.18 (t, 2H), 3.15 (t, 2H), 6.92 (m, 3H). m/z (ESI) 428 [C18H30ClN7O3+H]+. mp 194-196° C.

Provenance & Evidence