Ethanol → HCID 178500880, compound

Participants

Reaction Conditions

Reaction Steps

Compound 103 (366 mg, 0.99 mmol) was dissolved in ethanol (8 mL) then diisopropylethyl amine (0.86 mL, 4.9 mmol) and 1-(3,5-diamino-6-chloropyrazine-2-methyl-isothiourea hydriodide (407 mg, 1.04 mmol) were added and the reaction was heated to 65° C. for 1.5 h. The solvents were removed under reduced pressure and the residue was purified by column chromatography (silica gel, eluent: 90:10:1, v/v dichloromethane/methanol/conc. ammonium hydroxide) to provide compound 104 (215 mg, 37%). 1H NMR (300 MHz, DMSO-d6) δ 9.13 (m, 1H), 8.89 (m, 1H), 8.70 (m, 1H), 7.45 (m, 4H), 7.13 (d, 2H), 6.85 (d, 2H), 4.43 (m, 1H), 4.17 (m, 2H), 3.68 (s, 3H), 3.30 (m, 2H), 2.90 (m, 1H), 2.56 (m, 2H), 1.58 (m, 4H), 1.40 (s, 9H). m/z (APCI) 579 [C25H35ClN8O6+H]+. Rf=0.65 (85:15:1 dichloromethane/methanol/conc. ammonium hydroxide).

Provenance & Evidence