To a stirred solution of the hydrochloride salt of 40c (140 mg, 0.506 mmol), and DIPEA (88.1 μL, 0.506 mmol) and DMF (5 mL) under nitrogen was added 70 (125 mg, 0.506 mmol) and HBTU (211 mg, 0.556 mmol) and the reaction was stirred at RT for 18 h. The reaction was poured into water and extracted with EtOAc. The combined extracts were dried (MgSO4) and evaporated and the crude material was purified by reverse phase chromatography (SP4) eluting with a MeCN/H2O gradient (10 to 95% MeCN) to afford 83.5 mg (35.2%) of N-((4-chloro-3-fluorophenyl)(1-methyl-1H-pyrazol-4-yl)methyl)-2-((S)-1-hydroxypropan-2-ylamino)quinazoline-7-carboxamide (I-1).
