Diisopropylethylamine → HCID 178512402, compound

Participants

Reaction Conditions

Reaction Steps

Diisopropylethylamine (0.26 mL, 1.49 mmol) was added to a solution of 12-aminododecanoic acid (1H-imidazol-2-yl)amide dihydrochloride (14) (0.056 mg, 0.16 mmol) in absolute ethanol (5 mL). A white precipitate formed and the reaction was stirred at 70° C. for 10 min, then 1-(3,5-diamino-6-chloropyrazine-2-carbonyl)-2-methylisothiourea hydriodide (0.087 g, 0.22 mmol) was added in one portion. The reaction mixture was stirred at this temperature for 16 hours then cooled to room temperature. The solvent was removed by rotary evaporation and the resulting residue was dissolved in small volume of methanol and the solution passed through an ion exchange resin column (Dowex 550A OH type). The resin was rinsed with methanol and the methanol solution was concentrated in vacuo. The resulting residue was purified by Biotage silica gel column chromatography eluting with 1% to 10% of 9:1 methanol/ammonium hydroxide in dichloromethane to give 12-[N′-(3,5-diamino-6-chloropyrazine-2-carbonyl)guanidino]dodecanoic acid (1H-imidazol-2-yl)amide 15 (0.034 g, 44%) as a yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 1.25 (m, 14H), 1.50 (m, 4H), 2.29 (t, 2H), 3.09 (m, 2H), 6.61 (m, 4H). m/z (ESI) 493 [C21H33ClN10O2+H]+. mp 102-104° C.

Provenance & Evidence