Diisopropylethylamine → HCID 178512147, compound

Participants

Reaction Conditions

Reaction Steps

A solution containing 66 (45 mg, 0.08 mmol) dissolved in ethanol (4 mL) was heated to 65° C. The reaction mixture was treated with 1-(3,5-diamino-6-chloropyrazine-2-carbonyl)-2-methylisothiourea hydriodide (32 mg, 0.12 mmol) and diisopropylethylamine (0.40 μL). The reaction mixture was stirred at that temperature for 5 h under N2 atmosphere. The solution was concentrated in 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 67 (18 mg, 30%) as a pale yellow solid: 1H NMR (500 MHz, DMSO-d6) δ 7.26 (s, 1H), 7.10 (s, 2H), 6.97 (s, 1H), 6.68 (s, 1H), 6.58 (s, 1H), 4.88 (br, 1H), 4.46 (s, 3H), 3.16 (s, 2H), 1.58-1.23 (m, 6H); m/z (ESI) 766 [C39H53ClN8O7+H]+.

Provenance & Evidence