1,2-Dichloroethane → HCID 178481748, compound

Participants

Reaction Steps

In a 100 mL round-bottomed flask, 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (0.150 g, 0.295 mmol), EDC (61 mg, 0.32 mmol), DIEA (52 μl, 0.295 mmol) were combined with dichloromethane (3 ml) to give a yellow solution. Stirred for 30 min then trans-4-aminocyclohexanol (48 mg, 0.42 mmol) was added. The reaction mixture was stirred at room temperature for 24 h then diluted with dichloromethane and washed with water. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 0% to 5% MeOH in DCM) and recrystallized from ethyl acetate to afford 60 mg of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (trans-4-hydroxy-cyclohexyl)amide as a white solid. MS: [M+H]+=555.

Provenance & Evidence