Triethylamine → (S)-3-tert-Butoxycarbonylamino-2-[(4-methyl-2-{2-[1-(tetrahydro-pyran-2-yl)-1H-indazol-4-yl]-acetylamino}-thiazole-5-carbonyl)-amino]-propionic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-Methyl-2-{2-[1-(tetrahydro-pyran-2-yl)-1H-indazol-4-yl]-acetylamino}-thiazole-5-carboxylic acid (540 mg, 1.348 mmol) in anhydrous DMF (25 mL) was added HBTU (614 mg, 1.619 mmol), HOBt (219 mg, 1.621 mmol), H-DAP(BOC)-OME HCL (515 mg, 2.022 mmol) and triethylamine (0.9 mL, 6.457 mmol). The reaction mixture was stirred at 25° C. for 1 h and concentrated under reduced pressure to remove most of the DMF. The residue was diluted with ethyl acetate (200 mL), washed with 1/1 water/brine (40 mL), aqueous 1N HCl (40 mL), brine (40 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The resulting crude compound was purified by flash chromatography (40% to 100% EtOAc in hexanes) to give (S)-3-tert-Butoxycarbonylamino-2-[(4-methyl-2-{2-[1-(tetrahydropyran-2-yl)-1H-indazol-4-yl]-acetylamino}-thiazole-5-carbonyl)-amino]-propionic acid methyl ester (548.6 mg, 68%) as an off white foam. MS m/e 617.4 (M+H+).

Provenance & Evidence