Trifluoroacetic acid → HCID 86656421, compound

Participants

Reaction Steps

tert-Butyl cis-3-(7-(5-methoxy-1-methyl-1H-indol-3-yl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)cyclopentylcarbamate (0.331 g, 0.524 mmol, prepared using J.1 from Preparation #I.1 with cis-3-(tert-butoxycarbonylamino)cyclopentanecarboxylic acid [Peptech], and L.1 with mercury(II) trifluoroacetate) in DCM (8 mL) was treated with TFA (2.0 mL, 26 mmol) then stirred for about 1.5 h at rt. The solvents were removed under reduced pressure then the material was dissolved in 1,4-dioxane (4 mL) and treated with concentrated aqueous NH4OH (2.5 mL, 24 mmol). The mixture was heated at about 60° C. for about 30 min. The mixture was concentrated under reduced pressure then dissolved in AcOH (1 mL) and DMF (3.5 mL) then the material was purified by preparative reverse phase HPLC (Table 2, Method i) to give cis-3-(7-(5-methoxy-1-methyl-1H-indol-3-yl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)cyclopentanamine diacetate (0.145 g, 53%): LC/MS (Table 2, Method a) Rt=1.73 min; MS m/z 401.2 (M+H)+. Syk IC50=A.

Provenance & Evidence