Diisopropylethylamine → HCID 178442121, compound

Participants

Reaction Conditions

Reaction Steps

Diisopropylethylamine (0.45 mL, 2.58 mmol) was added to a mixture of amino alcohol 142 (0.63 g, 1.69 mmol) and 1-(3,5-diamino-6-chloropyrazine-2-carbonyl)-2-methylisothiourea hydriodide (0.66 g, 2.58 mmol) in absolute ethanol (10 mL). The mixture was stirred at 75° C. (oil bath) for 4.5 h. After this time the mixture was cooled to rt and the solvent was removed by rotary evaporation. Purification by column chromatography (silica gel, a gradient of 5:95 to 10:90 methanol/dichloromethane, followed by a gradient of 5:95 to 10:90 (10% concentrated aqueous ammonium hydroxide/methanol)/dichloromethane) and subsequent drying in a 40° C. vacuum oven for 88 h afforded the phenol derivative 143 (0.30 g, 30% yield) as a yellow solid: mp 82-86° C.; 1H NMR (500 MHz, DMSO-d6) δ 0.93 (dd, 3H, J=6.0, 3.5 Hz), 1.21-1.28 (m, 1H), 1.32-1.40 (m, 1H), 1.49-1.60 (m, 6H), 1.75 (s, 1H), 2.49-2.66 (m, 5H), 3.11-3.19 (m, 2H), 4.44-4.48 (m, 1H), 5.17 (br s, 1H), 6.59-6.72 (m, 6H), 7.06-7.11 (m, 5H), 9.09 (br s, 1H); m/z (ESI) 583 [C29H39ClN8O3+H]+.

Provenance & Evidence