Water → HCID 58382004, compound

Participants

Reaction Steps

To a mixture of 7-(5-methoxy-1-methyl-1H-indol-3-yl)-1-(tetrahydro-2H-pyran-3-yl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.245 g, 0.461 mmol; prepared using J.1 from Preparation #I.1 with tetrahydro-2H-pyran-2-carboxylic acid [Acella], and L.1 with mercury(II) trifluoroacetate) in DCM (5 mL) was added TFA (0.887 mL, 11.5 mmol). After stirring at rt for about 15 h, the mixture was concentrated in vacuo. The material was dissolved in MeOH (5 mL) and then treated with a 30% aqueous NH4OH solution (1.79 mL, 13.8 mmol). The mixture was heated to about 60° C. for about 1 h then cooled to rt. Water was added (10 mL) and the solids were collected by filtration then washed with water (10 mL). The material was dried in a vacuum oven at about 60° C. for about 16 h to provide 7-(5-methoxy-1-methyl-1H-indol-3-yl)-1-(tetrahydro-2H-pyran-3-yl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.072 g, 39%): LC/MS (Table 2, Method a) Rt=2.16 min; MS m/z 402 (M+H)+. Syk IC50=A.

Provenance & Evidence