Diisopropylethylamine → 2-(5-cyclopropyl-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-2-methoxy-1-methyl-ethyl)-amide

Participants

Reaction Steps

A 25 mL round-bottomed flask was charged with 2-(5-cyclopropyl-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (70 mg, 0.15 mmol), (S)-1-methoxypropan-2-amine hydrochloride (21 mg, 0.16 mmol), and HATU (63 mg, 0.16 mmol). Then added acetonitrile (2 mL) followed by N,N-diisopropylethylamine (0.08 mL, 0.45 mmol). The reaction mixture was stirred at room temperature overnight then quenched with water. The mixture was extracted with ethyl acetate (3×). The organic layers were combined, dried over Na2SO4, and concentrated. The crude material was purified by flash chromatography over silica gel (gradient: 15% to 100% EtOAc in heptane) to afford 34 mg (42%) of 2-(5-cyclopropyl-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-2-methoxy-1-methyl-ethyl)-amide as a white solid.

Provenance & Evidence