HCID 58382335, compound → HCID 58382165, compound

Participants

Reaction Conditions

Reaction Steps

MeMgCl (3 M in THF, 0.54 mL, 1.6 mmol) was added to THF (3 mL) then cooled to about −20° C. 1-(4-(1-Ethyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-2-yl)phenyl)ethanone (0.062 g, 0.204 mmol) was suspended in THF (3 mL) then added to the MeMgCl solution with stirring while maintaining the temperature of the mixture at about −15 to −20° C. The flask with the 1-(4-(1-ethyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-2-yl)phenyl)ethanone was rinsed with THF (2 mL) then this solution was also added to the MeMgCl mixture. The mixture was stirred for about 10 min then AcOH (1 mL) was added. The material was purified in two equal portions by preparative reverse phase HPLC (Table 2, method j). The fractions from the preparative HPLC containing the title compound were concentrated under reduced pressure to remove most or all of the 1,4-dioxane. The mixture was basified with saturated aqueous NaHCO3 and the solids collected by filtration. The material was dried overnight under vacuum at about 60° C. to give 2-(4-(1-ethyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-2-yl)phenyl)propan-2-ol (0.033 g, 51%): LC/MS (Table 2, Method a) Rt=1.85 min; MS m/z 321 (M+H)+. Syk IC50=B

Provenance & Evidence