Ethanol → HCID 178512146, compound

Participants

Reaction Conditions

Reaction Steps

A solution containing 62 (0.24 g, 0.62 mmol) dissolved in ethanol (8 mL) was heated to 65° C. The reaction mixture was treated with 1-(3,5-diamino-6-chloropyrazine-2-carbonyl)-2-methylisothiourea hydriodide (0.24 mg, 0.62 mmol) and diisopropylethylamine (0.47 mL). The reaction mixture was stirred at that temperature for 5 h under N2 atmosphere. The solution was concentrated vacuo. The resulting residue was first purified by column chromatography eluting with a mixture of 0-20% (10% concentrated ammonium hydroxide in methanol) and dichloromethane, and then further purified by preparative TLC using the same solvent system to afford the desired product 63 (15 mg, 5%) as a pale yellow solid: 1H NMR (500 MHz, DMSO-d6) δ 7.22 (d, 1H), 7.08 (d, 4H), 6.97 (d, 1H), 6.68 (d, 4H), 6.57 (br, 1H), 4.45 (s, 2H), 3.15 (d, 2H), 2.33 (t, 1H), 1.59-1.52 (m, 6H), 1.39 (s, 2H), 1.23 (s, 1H), m/z (ESI) 600 [C29H39ClN8O4+H]+.

Provenance & Evidence