Diisopropylamine → HCID 178516977, compound

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 1-(trans-3-aminocyclobutyl)-3-cyclopropyl-1H-imidazo[4,5-b]pyrazin-2(3H)-one hydrochloride (Intermediate 79, 0.1283 g, 0.455 mmol), 2-chloro-6-fluorobenzo[d]thiazole (0.094 g, 0.501 mmol, Step 1), DMAP (0.056 g, 0.455 mmol, Sigma-Aldrich Chemical Company, Inc.), and diisopropylamine (0.238 ml, 1.366 mmol, Sigma-Aldrich Chemical Company, Inc.) in DMSO (1.518 ml) and heated to 90° C. for 20 h. The crude product was purified by reverse-phase preparative HPLC using a Phenomenex Gemini column, 10 micron, C18, 110 Å, 100×50 mm, 0.1% TFA in CH3CN/H2O, gradient 10% to 90% over 12 min. Fractions containing product peak were concentrated in vacuo. The product was taken up in DCM and loaded onto a Silicyle Si-carbonate cartridge to remove any salts to give the title compound (61.2 mg, 0.154 mmol, 33.9% yield). LCMS showed product peak at 1.732 min (m+1=397.0).

Provenance & Evidence